Dehydrogenative Cross-Coupling of α,β-Unsaturated Compounds with Unactivated Olefins via Co(III) Catalysis

An oxidative cross-coupling of α,β-unsaturated compounds with unactivated alkenes via cobalt-catalyzed vinylic C–H activation has been developed. The present catalytic reaction was examined with various differently functionalized unsaturated compounds and unactivated olefins. In these reactions, hig...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 25; no. 34; pp. 6284 - 6289
Main Authors Logeswaran, Ravichandran, Jeganmohan, Masilamani
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.09.2023
Amer Chemical Soc
Subjects
Online AccessGet full text

Cover

Loading…
Abstract An oxidative cross-coupling of α,β-unsaturated compounds with unactivated alkenes via cobalt-catalyzed vinylic C–H activation has been developed. The present catalytic reaction was examined with various differently functionalized unsaturated compounds and unactivated olefins. In these reactions, highly valuable amide functionalized butadienes and indenones were prepared in good to excellent yields. A possible reaction mechanism is proposed involving directed olefinic C–H activation through a base-assisted deprotonation pathway.
AbstractList An oxidative cross-coupling of α,β-unsaturated compounds with unactivated alkenes via cobalt-catalyzed vinylic C–H activation has been developed. The present catalytic reaction was examined with various differently functionalized unsaturated compounds and unactivated olefins. In these reactions, highly valuable amide functionalized butadienes and indenones were prepared in good to excellent yields. A possible reaction mechanism is proposed involving directed olefinic C–H activation through a base-assisted deprotonation pathway.
An oxidative cross-coupling of & alpha;,& beta;-unsaturatedcompoundswith unactivated alkenes via cobalt-catalyzed vinylic C-Hactivation has been developed. The present catalytic reaction wasexamined with various differently functionalized unsaturated compoundsand unactivated olefins. In these reactions, highly valuable amidefunctionalized butadienes and indenones were prepared in good to excellentyields. A possible reaction mechanism is proposed involving directedolefinic C-H activation through a base-assisted deprotonationpathway.
Author Logeswaran, Ravichandran
Jeganmohan, Masilamani
AuthorAffiliation Department of Chemistry
AuthorAffiliation_xml – name: Department of Chemistry
Author_xml – sequence: 1
  givenname: Ravichandran
  surname: Logeswaran
  fullname: Logeswaran, Ravichandran
– sequence: 2
  givenname: Masilamani
  orcidid: 0000-0002-7835-3928
  surname: Jeganmohan
  fullname: Jeganmohan, Masilamani
  email: mjeganmohan@iitm.ac.in
BookMark eNqNkM1O4zAQx60Vq-XzCbjkCFpSxnbSxEeU5aMSEpftOXLsSTFK7WI7oD4WPAjPhEsrjqs9eWT_fzPj3yHZs84iIacUJhQYvZQqTJxfDBjjhCtgIMof5ICWjOcVlGzvu57CPjkM4QmAphvxi-zzagq8EMUBGf7g41p7t0Aro3nBrPEuhLxx42owdpG5Pvt4u_h4z-c2yDh6GVFnjVuu3Gh1yF5NfMzmVqrEfj09DNgbG7IXI1PsbDabnWeNjHJYBxOOyc9eDgFPducRmd9c_23u8vuH21lzdZ9LVrGY9yAkR6F1pUoQdQVKdRqlLjs91ZoX06IoECnXBZMUtOwUq6HvhFJ9LbhGfkTOtn1X3j2PGGK7NEHhMEiLbgwtq8tCVEmHSFG-jarNvz327cqbpfTrlkK70dwmze1Oc7vTnKh6S71i5_qgDFqF32RqDCUtgacRqW5MTGqdTU5tTOjv_0dT-nKb3mzx5EZvk7d_rvYJicGoDQ
Cites_doi 10.1039/c1cs15083a
10.1002/asia.201403224
10.1021/ol202580e
10.1021/cr100209d
10.1039/c1gc15875a
10.1021/acs.chemrev.2c00032
10.1039/c6cc05330k
10.1021/ja508165a
10.1039/c2cc36137j
10.1021/acs.orglett.1c01797
10.1039/d0cs00447b
10.1002/ejoc.201601253
10.1039/c7cc07777g
10.1002/anie.201512018
10.1021/acs.orglett.7b01415
10.1021/ol502005g
10.1021/acs.chemrev.9b00634
10.1021/acs.orglett.7b00825
10.1021/acscatal.6b01360
10.1021/cr500431s
10.1021/ar000209h
10.1021/cr900184e
10.1021/jacs.6b10309
10.1002/anie.201710601
10.1021/ar200185g
10.1055/s-0039-1690866
10.1021/acscatal.0c01436
10.1002/chem.201101340
10.1021/acs.orglett.0c02410
10.1021/ol102890k
10.1021/acscatal.0c03743
10.1002/chem.201501232
10.1002/anie.201209226
10.1021/cr300153J
10.1021/jacs.5b13353
10.1039/c7cc03213g
10.1021/acs.orglett.9b02717
10.1039/c7sc04827k
10.1039/d0sc05555g
10.1002/adsc.202200193
10.1002/adsc.201701162
10.1002/adsc.201500697
10.1021/acscatal.5b02218
10.1021/cr100280d
10.1021/acscatal.1c05869
10.1021/acscatal.5b02344
10.1021/acs.orglett.6b02229
10.1021/acscatal.6b01816
10.1039/c6cc07064g
10.1021/ja106814p
10.1021/acscatal.9b00655
10.1039/c6cc04835h
10.1002/anie.201906075
10.1021/ja5082734
10.1021/ja512237d
10.1002/anie.201303916
10.1021/acs.chemrev.9b00495
10.1039/C7CC07777G
10.1039/C6CC07064G
10.1021/cr300153j
10.1039/C6CC05330K
10.1039/C7CC03213G
10.1039/C6CC04835H
10.1039/D0CS00447B
10.1039/C7SC04827K
10.1039/D0SC05555G
ContentType Journal Article
Copyright 2023 American Chemical Society
Copyright_xml – notice: 2023 American Chemical Society
DBID 1KM
1KN
BLEPL
BNZSX
DTL
AAYXX
CITATION
7X8
DOI 10.1021/acs.orglett.3c02095
DatabaseName Index Chemicus
Current Chemical Reactions
Web of Science Core Collection
Web of Science - Science Citation Index Expanded - 2023
Science Citation Index Expanded
CrossRef
MEDLINE - Academic
DatabaseTitle Web of Science
CrossRef
MEDLINE - Academic
DatabaseTitleList
Web of Science
Database_xml – sequence: 1
  dbid: 1KN
  name: Current Chemical Reactions
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1523-7052
EndPage 6289
ExternalDocumentID 10_1021_acs_orglett_3c02095
001051503700001
h76347151
GrantInformation_xml – fundername: DST-SERB; Department of Science & Technology (India); Science Engineering Research Board (SERB), India
  grantid: CRG/2022/0003261
– fundername: CSIR; Council of Scientific & Industrial Research (CSIR) - India
GroupedDBID ---
-DZ
-~X
.K2
123
4.4
55A
5VS
6P2
7~N
AABXI
ABFRP
ABMVS
ABPTK
ABQRX
ABUCX
ACGFS
ACS
ADHLV
AEESW
AENEX
AFEFF
AHGAQ
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
BAANH
CS3
DU5
EBS
ED~
F5P
FDB
GGK
GNL
IH9
IHE
JG~
P2P
RNS
ROL
TN5
UI2
VF5
VG9
W1F
YNT
1KM
1KN
53G
AAHBH
AALRI
AAXUO
ABJNI
BLEPL
CUPRZ
DTL
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
AAYXX
CITATION
7X8
ID FETCH-LOGICAL-a272t-f09a3e9dd7c509870ccbdead5bd6dd346444ee13d42a10dabc280fb9ccf893de3
IEDL.DBID ACS
ISICitedReferencesCount 0
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=001051503700001
ISSN 1523-7060
IngestDate Fri Aug 16 14:01:32 EDT 2024
Fri Aug 23 04:10:21 EDT 2024
Wed Sep 18 08:10:13 EDT 2024
Fri Oct 04 21:06:01 EDT 2024
Mon Sep 04 05:32:46 EDT 2023
IsPeerReviewed true
IsScholarly true
Issue 34
Keywords OXIDATIVE OLEFINATION
FUNCTIONALIZATION
ACTIVATION
BONDS
C-H OLEFINATION
ELECTRON-DEFICIENT ALKENES
EFFICIENT
ACCESS
ALKENYLATION
AMIDES
Language English
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-a272t-f09a3e9dd7c509870ccbdead5bd6dd346444ee13d42a10dabc280fb9ccf893de3
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ORCID 0000-0002-7835-3928
PMID 37603494
PQID 2854970019
PQPubID 23479
PageCount 6
ParticipantIDs webofscience_primary_001051503700001CitationCount
crossref_primary_10_1021_acs_orglett_3c02095
acs_journals_10_1021_acs_orglett_3c02095
webofscience_primary_001051503700001
proquest_miscellaneous_2854970019
PublicationCentury 2000
PublicationDate 2023-09-01
PublicationDateYYYYMMDD 2023-09-01
PublicationDate_xml – month: 09
  year: 2023
  text: 2023-09-01
  day: 01
PublicationDecade 2020
PublicationPlace WASHINGTON
PublicationPlace_xml – name: WASHINGTON
PublicationTitle Organic letters
PublicationTitleAbbrev ORG LETT
PublicationTitleAlternate Org. Lett
PublicationYear 2023
Publisher American Chemical Society
Amer Chemical Soc
Publisher_xml – name: American Chemical Society
– name: Amer Chemical Soc
References Wencel-Delord, J (WOS:000293858500016) 2011; 40
Yang, JF (WOS:000471212600095) 2019; 9
Gandeepan, P (WOS:000373006100028) 2016; 55
Deb, A (WOS:000392459300035) 2017; 139
Yeung, CS (WOS:000288820600003) 2011; 111
Rej, S (WOS:000514255200005) 2020; 120
Zhang, J (WOS:000310068800020) 2012; 48
Besset, T (WOS:000292208900005) 2011; 17
Yoshino, T (WOS:000314998500012) 2013; 52
Sen, M (WOS:000406356500004) 2017; 19
Arockiam, PB (WOS:000296450100006) 2011; 13
Engle, KM (WOS:000305321100003) 2012; 45
Liu, C (WOS:000366005400002) 2015; 115
Jiang, B (WOS:000419110500032) 2018; 57
Nareddy, P (WOS:000379457300085) 2016; 6
Xue, X (WOS:000371665800012) 2016; 358
Ali, W (WOS:000625958900002) 2021; 12
Tsai, AS (WOS:000286577600049) 2011; 13
Zhang, J (WOS:000569377600038) 2020; 22
Keerthana, MS (WOS:000535936100010) 2020; 52
Padala, K (WOS:000297274700003) 2011; 13
Yu, CB (WOS:000391954000009) 2017; 53
Manikandan, R (WOS:000407169500002) 2017; 53
Yamaguchi, T (WOS:000381473200007) 2016; 52
Achar, TK (WOS:000598140200002) 2020; 10
Zhao, Q (WOS:000517360300001) 2020; 120
Nallagonda, R (WOS:000422659800007) 2018; 360
Li, TY (WOS:000489200100019) 2019; 21
Kong, WJ (WOS:000371103900019) 2016; 138
Le Bras, J (WOS:000288820600002) 2011; 111
Zhang, J (WOS:000629731800009) 2021; 50
Park, H (WOS:000478735900041) 2019; 58
Zeng, L (WOS:000400123600059) 2017; 19
Gandeepan, P (WOS:000351623600003) 2015; 10
Manikandan, R (WOS:000367706800026) 2016; 6
Grigorjeva, L (WOS:000341344600086) 2014; 16
Maity, S (WOS:000381236700076) 2016; 6
Logeswaran, R (WOS:000684033200017) 2021; 23
Manoharan, R (WOS:000382120300017) 2016; 52
Arockiam, PB (WOS:000311239600009) 2012; 112
Gao, K (WOS:000281460100035) 2010; 132
Lyons, TW (WOS:000274705900016) 2010; 110
Deb, A (WOS:000342608800034) 2014; 136
Logeswaran, R (WOS:000800617500001) 2022; 364
Moselage, M (WOS:000369774900002) 2016; 6
Bera, SS (WOS:000773693300038) 2022; 12
Zhu, RY (WOS:000342328200031) 2014; 136
Takahama, Y (WOS:000355762900015) 2015; 21
Li, TY (WOS:000416804400014) 2017; 53
Hu, XH (WOS:000351187200005) 2015; 137
Lu, MZ (WOS:000424010600025) 2018; 9
Deb, A (WOS:000395788100001) 2017; 2017
Lu, MZ (WOS:000906917700001) 2022; 122
Dhawa, U (WOS:000538766900050) 2020; 10
Li, FF (WOS:000383640600035) 2016; 18
Jia, CG (WOS:000170711300003) 2001; 34
Saini, V (WOS:000328677400009) 2013; 52
ref1/cit1d
ref2/cit2f
ref2/cit2e
ref2/cit2d
ref2/cit2c
ref2/cit2b
ref2/cit2a
ref1/cit1a
ref1/cit1c
ref1/cit1b
ref5/cit5b
ref5/cit5c
ref5/cit5a
ref7/cit7f
ref7/cit7e
ref7/cit7d
ref3/cit3b
ref3/cit3c
ref3/cit3a
ref3/cit3d
ref7/cit7c
ref7/cit7b
ref7/cit7a
ref5/cit5f
ref5/cit5d
ref5/cit5e
ref9/cit9c
ref10/cit10d
ref9/cit9b
ref10/cit10e
ref9/cit9a
ref8/cit8a
ref10/cit10a
ref8/cit8c
ref10/cit10b
ref8/cit8b
ref10/cit10c
ref8/cit8e
ref8/cit8d
ref8/cit8g
ref8/cit8f
ref9/cit9g
ref9/cit9f
ref9/cit9e
ref9/cit9d
ref6/cit6d
ref4/cit4a
ref6/cit6e
ref4/cit4b
ref6/cit6f
ref4/cit4c
ref6/cit6g
ref4/cit4d
ref4/cit4e
ref6/cit6a
ref4/cit4f
ref6/cit6b
ref6/cit6c
References_xml – volume: 40
  start-page: 4740
  year: 2011
  ident: WOS:000293858500016
  article-title: Towards mild metal-catalyzed C-H bond activation
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/c1cs15083a
  contributor:
    fullname: Wencel-Delord, J
– volume: 10
  start-page: 824
  year: 2015
  ident: WOS:000351623600003
  article-title: Transition-Metal-Catalyzed p-Bond-Assisted C-H Bond Functionalization: An Emerging Trend in Organic Synthesis
  publication-title: CHEMISTRY-AN ASIAN JOURNAL
  doi: 10.1002/asia.201403224
  contributor:
    fullname: Gandeepan, P
– volume: 13
  start-page: 6144
  year: 2011
  ident: WOS:000297274700003
  article-title: Ruthenium-Catalyzed Ortho-Alkenylation of Aromatic Ketones with Alkenes by C-H Bond Activation
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol202580e
  contributor:
    fullname: Padala, K
– volume: 111
  start-page: 1170
  year: 2011
  ident: WOS:000288820600002
  article-title: Intermolecular Dehydrogenative Heck Reactions
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr100209d
  contributor:
    fullname: Le Bras, J
– volume: 13
  start-page: 3075
  year: 2011
  ident: WOS:000296450100006
  article-title: Ruthenium diacetate-catalysed oxidative alkenylation of C-H bonds in air: synthesis of alkenyl N-arylpyrazoles
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/c1gc15875a
  contributor:
    fullname: Arockiam, PB
– volume: 122
  start-page: 17479
  year: 2022
  ident: WOS:000906917700001
  article-title: Recent Advances in Alkenyl sp2 C-H and C-F Bond Functionalizations: Scope, Mechanism, and Applications
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/acs.chemrev.2c00032
  contributor:
    fullname: Lu, MZ
– volume: 52
  start-page: 10129
  year: 2016
  ident: WOS:000381473200007
  article-title: Cobalt-catalyzed chelation assisted C-H allylation of aromatic amides with unactivated olefins
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c6cc05330k
  contributor:
    fullname: Yamaguchi, T
– volume: 136
  start-page: 13194
  year: 2014
  ident: WOS:000342328200031
  article-title: Ligand-Promoted Alkylation of C(sp3)-H and C(sp2)-H Bonds
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja508165a
  contributor:
    fullname: Zhu, RY
– volume: 48
  start-page: 11232
  year: 2012
  ident: WOS:000310068800020
  article-title: Ruthenium- and rhodium-catalyzed cross-coupling reaction of acrylamides with alkenes: efficient access to (Z,E)-dienamides
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c2cc36137j
  contributor:
    fullname: Zhang, J
– volume: 23
  start-page: 5679
  year: 2021
  ident: WOS:000684033200017
  article-title: Effect of Transition Metals on Chemodivergent Cross-Coupling of Acrylamides with Vinyl Acetate via C-H Activation
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.1c01797
  contributor:
    fullname: Logeswaran, R
– volume: 50
  start-page: 3263
  year: 2021
  ident: WOS:000629731800009
  article-title: Recent advances in chelation-assisted site- and stereoselective alkenyl C-H functionalization
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/d0cs00447b
  contributor:
    fullname: Zhang, J
– volume: 2017
  start-page: 1239
  year: 2017
  ident: WOS:000395788100001
  article-title: Emergence of Unactivated Olefins for the Synthesis of Olefinated Arenes
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1002/ejoc.201601253
  contributor:
    fullname: Deb, A
– volume: 53
  start-page: 12926
  year: 2017
  ident: WOS:000416804400014
  article-title: Ruthenium-catalyzed olefinic C-H alkenylation of enol-carbamates: highly stereo-selective synthesis of (Z,Z) and (Z,E)-butadienes
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c7cc07777g
  contributor:
    fullname: Li, TY
– volume: 55
  start-page: 4308
  year: 2016
  ident: WOS:000373006100028
  article-title: Diastereoselective [3+2] Annulation of Aromatic/Vinylic Amides with Bicyclic Alkenes through Cobalt-Catalyzed C-H Activation and Intramolecular Nucleophilic Addition
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201512018
  contributor:
    fullname: Gandeepan, P
– volume: 19
  start-page: 3699
  year: 2017
  ident: WOS:000406356500004
  article-title: Dehydrative Cp*Co(III)-Catalyzed C-H Bond Allenylation
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.7b01415
  contributor:
    fullname: Sen, M
– volume: 16
  start-page: 4684
  year: 2014
  ident: WOS:000341344600086
  article-title: Cobalt-Catalyzed, Aminoquinoline-Directed Coupling of sp2 C-H Bonds with Alkenes
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol502005g
  contributor:
    fullname: Grigorjeva, L
– volume: 120
  start-page: 1981
  year: 2020
  ident: WOS:000517360300001
  article-title: N-Heterocyclic Carbene Complexes in C-H Activation Reactions
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/acs.chemrev.9b00634
  contributor:
    fullname: Zhao, Q
– volume: 19
  start-page: 2170
  year: 2017
  ident: WOS:000400123600059
  article-title: Cobalt-Catalyzed Intramolecular Oxidative C(sp3)-H/N-H Carbonylation of Aliphatic Amides
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.7b00825
  contributor:
    fullname: Zeng, L
– volume: 6
  start-page: 4755
  year: 2016
  ident: WOS:000379457300085
  article-title: Ruthenium(II)-Catalyzed Regioselective C-H Arylation of Cyclic and N,N-Dialkyl Benzamides with Boronic Acids by Weak Coordination
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.6b01360
  contributor:
    fullname: Nareddy, P
– volume: 115
  start-page: 12138
  year: 2015
  ident: WOS:000366005400002
  article-title: Oxidative Coupling between Two Hydrocarbons: An Update of Recent C-H Functionalizations
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr500431s
  contributor:
    fullname: Liu, C
– volume: 34
  start-page: 633
  year: 2001
  ident: WOS:000170711300003
  article-title: Catalytic functionalization of arenes and alkanes via C-H bond activation
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar000209h
  contributor:
    fullname: Jia, CG
– volume: 110
  start-page: 1147
  year: 2010
  ident: WOS:000274705900016
  article-title: Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr900184e
  contributor:
    fullname: Lyons, TW
– volume: 139
  start-page: 763
  year: 2017
  ident: WOS:000392459300035
  article-title: Detailed Mechanistic Studies on Palladium-Catalyzed Selective C-H Olefination with Aliphatic Alkenes: A Significant Influence of Proton Shuttling
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.6b10309
  contributor:
    fullname: Deb, A
– volume: 57
  start-page: 555
  year: 2018
  ident: WOS:000419110500032
  article-title: Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201710601
  contributor:
    fullname: Jiang, B
– volume: 45
  start-page: 788
  year: 2012
  ident: WOS:000305321100003
  article-title: Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar200185g
  contributor:
    fullname: Engle, KM
– volume: 52
  start-page: 1625
  year: 2020
  ident: WOS:000535936100010
  article-title: Cobalt(III)-Catalyzed Redox-Neutral Coupling of Acrylamides with Activated Alkenes via C-H Bond Activation
  publication-title: SYNTHESIS-STUTTGART
  doi: 10.1055/s-0039-1690866
  contributor:
    fullname: Keerthana, MS
– volume: 10
  start-page: 6457
  year: 2020
  ident: WOS:000538766900050
  article-title: Cobalta-Electrocatalyzed C-H Allylation with Unactivated Alkenes
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.0c01436
  contributor:
    fullname: Dhawa, U
– volume: 17
  start-page: 7167
  year: 2011
  ident: WOS:000292208900005
  article-title: RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  doi: 10.1002/chem.201101340
  contributor:
    fullname: Besset, T
– volume: 22
  start-page: 6884
  year: 2020
  ident: WOS:000569377600038
  article-title: Ruthenium(II)-Catalyzed C-H Arylation of N,N-Dialkyl Thiobenzamides with Boronic Acids by Sulfur Coordination in 2-MeTHF
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.0c02410
  contributor:
    fullname: Zhang, J
– volume: 13
  start-page: 540
  year: 2011
  ident: WOS:000286577600049
  article-title: Rh(III)-Catalyzed Oxidative Coupling of Unactivated Alkenes via C-H Activation
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol102890k
  contributor:
    fullname: Tsai, AS
– volume: 10
  start-page: 13748
  year: 2020
  ident: WOS:000598140200002
  article-title: Transition Metal Catalyzed Enantioselective C(sp2)-H Bond Functionalization
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.0c03743
  contributor:
    fullname: Achar, TK
– volume: 21
  start-page: 9053
  year: 2015
  ident: WOS:000355762900015
  article-title: Oxidative Olefination of Anilides with Unactivated Alkenes Catalyzed by an (Electron-Deficient 5-Cyclopentadienyl)Rhodium(III) Complex Under Ambient Conditions
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  doi: 10.1002/chem.201501232
  contributor:
    fullname: Takahama, Y
– volume: 52
  start-page: 2207
  year: 2013
  ident: WOS:000314998500012
  article-title: A Cationic High-Valent Cp*CoIII Complex for the Catalytic Generation of Nucleophilic Organometallic Species: Directed C-H Bond Activation
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201209226
  contributor:
    fullname: Yoshino, T
– volume: 112
  start-page: 5879
  year: 2012
  ident: WOS:000311239600009
  article-title: Ruthenium(II)-Catalyzed C-H Bond Activation and Functionalization
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr300153J
  contributor:
    fullname: Arockiam, PB
– volume: 138
  start-page: 2146
  year: 2016
  ident: WOS:000371103900019
  article-title: Pd-Catalyzed α-Selective C-H Functionalization of Olefins: En Route to 4-Imino-β-Lactams
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.5b13353
  contributor:
    fullname: Kong, WJ
– volume: 53
  start-page: 8931
  year: 2017
  ident: WOS:000407169500002
  article-title: Recent advances in the ruthenium(II)-catalyzed chelation-assisted C-H olefination of substituted aromatics, alkenes and heteroaromatics with alkenes via the deprotonation pathway
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c7cc03213g
  contributor:
    fullname: Manikandan, R
– volume: 21
  start-page: 7772
  year: 2019
  ident: WOS:000489200100019
  article-title: Cobalt-Catalyzed Olefinic C-H Alkenylation/Alkylation Switched by Carbonyl Groups
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.9b02717
  contributor:
    fullname: Li, TY
– volume: 9
  start-page: 1311
  year: 2018
  ident: WOS:000424010600025
  article-title: Ligand-enabled ortho-C-H olefination of phenylacetic amides with unactivated alkenes
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c7sc04827k
  contributor:
    fullname: Lu, MZ
– volume: 12
  start-page: 2735
  year: 2021
  ident: WOS:000625958900002
  article-title: Recent development in transition metal-catalysed C-H olefination
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/d0sc05555g
  contributor:
    fullname: Ali, W
– volume: 364
  start-page: 2113
  year: 2022
  ident: WOS:000800617500001
  article-title: Transition-Metal-Catalyzed, Chelation-Assisted C-H Alkenylation and Allylation of Organic Molecules with Unactivated Alkenes
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.202200193
  contributor:
    fullname: Logeswaran, R
– volume: 360
  start-page: 255
  year: 2018
  ident: WOS:000422659800007
  article-title: Cobalt-Catalyzed Diastereoselective [4+2] Annulation of Phosphinamides with Heterobicyclic Alkenes at Room Temperature
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.201701162
  contributor:
    fullname: Nallagonda, R
– volume: 358
  start-page: 573
  year: 2016
  ident: WOS:000371665800012
  article-title: Rhodium(III)-Catalyzed Direct C-H Olefination of Arenes with Aliphatic Olefins
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.201500697
  contributor:
    fullname: Xue, X
– volume: 6
  start-page: 230
  year: 2016
  ident: WOS:000367706800026
  article-title: Ruthenium-Catalyzed ortho Alkenylation of Aromatics with Alkenes at Room Temperature with Hydrogen Evolution
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.5b02218
  contributor:
    fullname: Manikandan, R
– volume: 111
  start-page: 1215
  year: 2011
  ident: WOS:000288820600003
  article-title: Catalytic Dehydrogenative Cross-Coupling: Forming Carbon-Carbon Bonds by Oxidizing Two Carbon-Hydrogen Bonds
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr100280d
  contributor:
    fullname: Yeung, CS
– volume: 12
  start-page: 3111
  year: 2022
  ident: WOS:000773693300038
  article-title: Cobalt-N-Heterocyclic Carbene Complexes in Catalysis
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.1c05869
  contributor:
    fullname: Bera, SS
– volume: 6
  start-page: 498
  year: 2016
  ident: WOS:000369774900002
  article-title: Cobalt-Catalyzed C-H Activation
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.5b02344
  contributor:
    fullname: Moselage, M
– volume: 18
  start-page: 4582
  year: 2016
  ident: WOS:000383640600035
  article-title: Olefination of Electron-Deficient Alkenes with Allyl Acetate: Stereo- and Regioselective Access to (2Z,4E)-Dienamides
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.6b02229
  contributor:
    fullname: Li, FF
– volume: 6
  start-page: 5493
  year: 2016
  ident: WOS:000381236700076
  article-title: Switch to Allylic Selectivity in Cobalt-Catalyzed Dehydrogenative Heck Reactions with Unbiased Aliphatic Olefins
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.6b01816
  contributor:
    fullname: Maity, S
– volume: 53
  start-page: 533
  year: 2017
  ident: WOS:000391954000009
  article-title: A direct cross-coupling reaction of electron-deficient alkenes using an oxidizing directing group
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c6cc07064g
  contributor:
    fullname: Yu, CB
– volume: 132
  start-page: 12249
  year: 2010
  ident: WOS:000281460100035
  article-title: Cobalt-Catalyzed Hydroarylation of Alkynes through Chelation-Assisted C-H Bond Activation
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja106814p
  contributor:
    fullname: Gao, K
– volume: 9
  start-page: 5638
  year: 2019
  ident: WOS:000471212600095
  article-title: Cobalt-Catalyzed Enantioselective and Chemodivergent Addition of Cyclopropanols to Oxabicyclic Alkenes
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.9b00655
  contributor:
    fullname: Yang, JF
– volume: 52
  start-page: 10533
  year: 2016
  ident: WOS:000382120300017
  article-title: Cobalt-catalyzed C-H olefination of aromatics with unactivated alkenes
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c6cc04835h
  contributor:
    fullname: Manoharan, R
– volume: 58
  start-page: 11424
  year: 2019
  ident: WOS:000478735900041
  article-title: Utilizing Carbonyl Coordination of Native Amides for Palladium-Catalyzed C(sp3)-H Olefination
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201906075
  contributor:
    fullname: Park, H
– volume: 136
  start-page: 13602
  year: 2014
  ident: WOS:000342608800034
  article-title: Palladium-Catalyzed Aryl C-H Olefination with Unactivated, Aliphatic Alkenes
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja5082734
  contributor:
    fullname: Deb, A
– volume: 137
  start-page: 3169
  year: 2015
  ident: WOS:000351187200005
  article-title: Stereo- and Chemoselective Cross-Coupling between Two Electron-Deficient Acrylates: An Efficient Route to (Z,E)-Muconate Derivatives
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja512237d
  contributor:
    fullname: Hu, XH
– volume: 52
  start-page: 11206
  year: 2013
  ident: WOS:000328677400009
  article-title: Transition-Metal-Catalyzed Laboratory-Scale Carbon-Carbon Bond-Forming Reactions of Ethylene
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201303916
  contributor:
    fullname: Saini, V
– volume: 120
  start-page: 1788
  year: 2020
  ident: WOS:000514255200005
  article-title: Bidentate Directing Groups: An Efficient Tool in C-H Bond Functionalization Chemistry for the Expedient Construction of C-C Bonds
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/acs.chemrev.9b00495
  contributor:
    fullname: Rej, S
– ident: ref10/cit10e
  doi: 10.1021/acs.orglett.9b02717
– ident: ref4/cit4b
  doi: 10.1021/cr900184e
– ident: ref10/cit10d
  doi: 10.1021/acs.orglett.1c01797
– ident: ref2/cit2e
  doi: 10.1021/acs.chemrev.9b00495
– ident: ref6/cit6b
  doi: 10.1021/ja5082734
– ident: ref1/cit1d
  doi: 10.1021/cr500431s
– ident: ref1/cit1c
  doi: 10.1021/cr100280d
– ident: ref8/cit8g
  doi: 10.1021/acs.orglett.7b00825
– ident: ref5/cit5a
  doi: 10.1021/acscatal.5b02344
– ident: ref8/cit8e
  doi: 10.1002/chem.201101340
– ident: ref10/cit10b
  doi: 10.1021/acs.chemrev.2c00032
– ident: ref9/cit9c
  doi: 10.1039/C7CC07777G
– ident: ref7/cit7a
  doi: 10.1002/adsc.202200193
– ident: ref9/cit9b
  doi: 10.1021/jacs.5b13353
– ident: ref1/cit1b
  doi: 10.1002/anie.201303916
– ident: ref3/cit3d
  doi: 10.1021/acscatal.6b01360
– ident: ref8/cit8c
  doi: 10.1021/ja512237d
– ident: ref6/cit6c
  doi: 10.1021/ol502005g
– ident: ref9/cit9e
  doi: 10.1039/C6CC07064G
– ident: ref9/cit9g
  doi: 10.1002/adsc.201701162
– ident: ref4/cit4a
  doi: 10.1021/cr300153j
– ident: ref5/cit5b
  doi: 10.1002/anie.201209226
– ident: ref4/cit4d
  doi: 10.1021/acscatal.0c03743
– ident: ref1/cit1a
  doi: 10.1021/ar000209h
– ident: ref6/cit6g
  doi: 10.1002/adsc.201500697
– ident: ref9/cit9d
  doi: 10.1055/s-0039-1690866
– ident: ref8/cit8b
  doi: 10.1039/c2cc36137j
– ident: ref4/cit4e
  doi: 10.1039/c1gc15875a
– ident: ref2/cit2c
  doi: 10.1002/asia.201403224
– ident: ref7/cit7d
  doi: 10.1039/C6CC05330K
– ident: ref2/cit2d
  doi: 10.1039/C7CC03213G
– ident: ref7/cit7e
  doi: 10.1039/C6CC04835H
– ident: ref10/cit10a
  doi: 10.1039/D0CS00447B
– ident: ref7/cit7c
  doi: 10.1021/acscatal.6b01816
– ident: ref5/cit5d
  doi: 10.1021/acs.orglett.0c02410
– ident: ref8/cit8f
  doi: 10.1021/acscatal.9b00655
– ident: ref4/cit4f
  doi: 10.1021/acs.orglett.7b01415
– ident: ref9/cit9f
  doi: 10.1002/anie.201512018
– ident: ref7/cit7b
  doi: 10.1002/ejoc.201601253
– ident: ref5/cit5e
  doi: 10.1021/acscatal.5b02218
– ident: ref5/cit5f
  doi: 10.1021/acscatal.1c05869
– ident: ref2/cit2a
  doi: 10.1021/cr100209d
– ident: ref5/cit5c
  doi: 10.1021/ja106814p
– ident: ref8/cit8a
  doi: 10.1039/D0CS00447B
– ident: ref8/cit8d
  doi: 10.1021/ja508165a
– ident: ref6/cit6d
  doi: 10.1039/C7SC04827K
– ident: ref6/cit6e
  doi: 10.1002/chem.201501232
– ident: ref3/cit3a
  doi: 10.1039/D0SC05555G
– ident: ref3/cit3c
  doi: 10.1021/ol202580e
– ident: ref2/cit2b
  doi: 10.1039/c1cs15083a
– ident: ref4/cit4c
  doi: 10.1021/ar200185g
– ident: ref6/cit6f
  doi: 10.1021/jacs.6b10309
– ident: ref2/cit2f
  doi: 10.1021/acs.chemrev.9b00634
– ident: ref7/cit7f
  doi: 10.1021/acscatal.0c01436
– ident: ref10/cit10c
  doi: 10.1021/acs.orglett.6b02229
– ident: ref3/cit3b
  doi: 10.1002/anie.201906075
– ident: ref6/cit6a
  doi: 10.1021/ol102890k
– ident: ref9/cit9a
  doi: 10.1002/anie.201710601
SSID ssj0011529
Score 2.476037
Snippet An oxidative cross-coupling of α,β-unsaturated compounds with unactivated alkenes via cobalt-catalyzed vinylic C–H activation has been developed. The present...
An oxidative cross-coupling of & alpha;,& beta;-unsaturatedcompoundswith unactivated alkenes via cobalt-catalyzed vinylic C-Hactivation has been developed. The...
Source Web of Science
SourceID proquest
crossref
webofscience
acs
SourceType Aggregation Database
Enrichment Source
Index Database
Publisher
StartPage 6284
SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Dehydrogenative Cross-Coupling of α,β-Unsaturated Compounds with Unactivated Olefins via Co(III) Catalysis
URI http://dx.doi.org/10.1021/acs.orglett.3c02095
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001051503700001
https://search.proquest.com/docview/2854970019
Volume 25
WOS 001051503700001
WOSCitedRecordID wos001051503700001
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3NbtQwEB7R5UAvBQqILT8yUg9FqpfEyWbjIwpUXaSWQ7tSb1HssduKKqmabKXyVvAg-0zMZJNSoEJ7jGNZ8czY88Xj-QZge4zkowNMZKHpdzW2OpHaOyXRmxSNik2IfKB_cJjsz-IvJ-OTO8nqf0XwVfihsDU_0yyaUWQJ3ejxGjxUfIeQkVB2dBs0IFekW3pUFUkmhelJhu4fhN2Rrf90R78x5j1eqPU4e4_hsM_bWV40-TaaN2Zkv_9L47jaZJ7ARoc9xcelsTyFB67chEdZX_LtGVx8cmc3eFWRUbV84CLjj5ZZNee83VNRebH4sbv4KWdlzYSghFNR8I7CtZlqwWe6YlZyqsR1--rrhfPnZS2uzwvqtjOdTt-LjM-LmAblOcz2Ph9n-7IrxyALNVGN9IEuIqcRJ5ZQBq1zaw2SIY4NJohRTMgqdi6MSPtFGGBhrEoDb7S1nkARuugFDMqqdC9BpLSp4sQoo5EpAE2aok-S1EU68YmLgyHskKTybjnVeRspV2HOjZ348k58Q9jtFZhfLgk6_t_9Xa_knITL0ZGidNW8zjmVVHMUXg9h-672b4dtq4kSgI4mbUxkCOEq3bKOa505Bpqt1Sf2Cta5tP3yPttrGDRXc_eGAFBj3rZm_ws_VgVj
link.rule.ids 315,786,790,2782,27109,27957,27958,57093,57143
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1LT9wwEB619EAv0Ke6fboSByrhJe_Exyot2m2BHkokblHscVpUlCCSRYJ_RX8Iv6kz3uzSVqiiV9uy7PHY89nj-QZgI0ay0R4mslJ0XY2MSqSqbSCx1hnqINI-8oP-3n4yKaJPh_HhEBTGsTA0iI566pwT_5pdwN8eymgy_Tg0BHJUfBfuxSndyBkQ5V-XvgOySMqxpAahZG6YBdfQzZ2wVTLdn1bpGmreYIyc4dlZh2I5ZPff5Md41uuxufiLzfF_5_QA1gYkKt7PVech3LHNI1jNFwngHsPxB_v9HE9bUjHHDi5yHrvM2xlH8X4TbS2uLreufsqi6ZgelFArCj5fOFNTJ_iFVxQNB06cuaovx7Y-ajpxdlRRs83pdPpO5Px6xKQoT6DY-XiQT-SQnEFWQRr0svZUFVqFmBrCHLTrjdFIahlrTBDDiHBWZK0fki5UvoeVNkHm1VoZUxNEQhs-hZWmbewzEBkdsZjqQCtkQkCdZVgnSWZDldSJjbwRbJKkymFzdaXzmwd-yYWD-MpBfCPYWqxjeTKn6_h387eLtS5JuOwrqRrbzrqSA0sV--TVCDZ-V4Jlty63KMHpMHUekhH4t2mWD8zrzDjQP7_9xN7A6uRgb7fcne5_fgH3Oen9_KfbS1jpT2f2FUGjXr92O-EXpLoNzg
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3bbtQwEB2VIkFfuKMuVyP1oUj1kvvGjyhl1eVSkGCl8hTFHhsqqqRqspXgr-BD-k3MeJPlogpVvDqWZY9nPCcezxmArRTJRweYyUrR72piVCaVs5FEp3PUUaJD5Av9N_vZ3jx5eZAerEE-5MLQJFoaqfVBfLbqY3Q9w0D4rG-nBXXj2BDQUekluJxyCW8GRcX7VfyAvJLyTKlRLJkfZuAbOn8Q9kym_dMz_YKb5zgk73ym1-Hjatr-zcmX8aLTY_PtL0bH_1nXDbjWI1LxfKlCN2HN1rfgajEUgrsNR7v281c8aUjVPEu4KHj-smgWnM37STROnH3fOfsh53XLNKGEXlHwOcMVm1rBN71iXnMCxan_9PbIusO6FaeHFXXbns1mT0XBt0hMjnIH5tMXH4o92RdpkFU0iTrpAlXFViFODGEPsn5jNJJ6phozxDghvJVYG8akE1UYYKVNlAdOK2McQSW08V1Yr5vaboLI6ajFiY60QiYG1HmOLstyG6vMZTYJRrBNkip7I2tLHz-PwpIbe_GVvfhGsDPsZXm8pO34d_cnw36XJFyOmVS1bRZtyQmmimPzagRbvyvCalhfY5RgdTzxkZIRhBfpVvQM7Mw80N27-MIew5V3u9Py9Wz_1X3YiAhxLR-8PYD17mRhHxJC6vQjbww_ARjOEEg
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Dehydrogenative+Cross-Coupling+of+%CE%B1%2C%CE%B2-Unsaturated+Compounds+with+Unactivated+Olefins+via+Co%28III%29+Catalysis&rft.jtitle=Organic+letters&rft.au=Logeswaran%2C+Ravichandran&rft.au=Jeganmohan%2C+Masilamani&rft.date=2023-09-01&rft.eissn=1523-7052&rft.volume=25&rft.issue=34&rft.spage=6284&rft.epage=6289&rft_id=info:doi/10.1021%2Facs.orglett.3c02095&rft.externalDBID=NO_FULL_TEXT
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1523-7060&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1523-7060&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1523-7060&client=summon