Synthesis of methylene-bridged α,β-unsaturated ketones: α-C sp 3 -H methylenation of aromatic ketones using Selectfluor as a mild oxidant

A three starting material four component reaction (3SM-4CR) is developed for the synthesis of α,β-unsaturated ketones and β-amino ketones in good yields. The reaction employs tetramethylethylenediamine (TMEDA) as a methylene and terminal olefin source, and Selectfluor as a mild oxidant. TMEDA worked...

Full description

Saved in:
Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 20; no. 2; pp. 415 - 419
Main Authors Zhang, Yuan, Liu, Zhiqi, Zhu, Tingyu, Huang, Ying, Fan, Weibin, Huang, Deguang
Format Journal Article
LanguageEnglish
Published England 05.01.2022
Online AccessGet full text

Cover

Abstract A three starting material four component reaction (3SM-4CR) is developed for the synthesis of α,β-unsaturated ketones and β-amino ketones in good yields. The reaction employs tetramethylethylenediamine (TMEDA) as a methylene and terminal olefin source, and Selectfluor as a mild oxidant. TMEDA worked as a dual synthon to provide two carbons in this metal-free transformation process. The scope and versatility of the methods have been demonstrated with 23 examples. A Selectfluor-promoted oxidative reaction mechanism is proposed based on the results of the experimental studies.
AbstractList A three starting material four component reaction (3SM-4CR) is developed for the synthesis of α,β-unsaturated ketones and β-amino ketones in good yields. The reaction employs tetramethylethylenediamine (TMEDA) as a methylene and terminal olefin source, and Selectfluor as a mild oxidant. TMEDA worked as a dual synthon to provide two carbons in this metal-free transformation process. The scope and versatility of the methods have been demonstrated with 23 examples. A Selectfluor-promoted oxidative reaction mechanism is proposed based on the results of the experimental studies.
Author Zhang, Yuan
Liu, Zhiqi
Huang, Ying
Zhu, Tingyu
Huang, Deguang
Fan, Weibin
Author_xml – sequence: 1
  givenname: Yuan
  surname: Zhang
  fullname: Zhang, Yuan
  email: dhuang@fjirsm.ac.cn
  organization: State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China
– sequence: 2
  givenname: Zhiqi
  surname: Liu
  fullname: Liu, Zhiqi
  email: dhuang@fjirsm.ac.cn
  organization: State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China
– sequence: 3
  givenname: Tingyu
  surname: Zhu
  fullname: Zhu, Tingyu
  email: dhuang@fjirsm.ac.cn
  organization: State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China
– sequence: 4
  givenname: Ying
  surname: Huang
  fullname: Huang, Ying
  email: dhuang@fjirsm.ac.cn
  organization: State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China
– sequence: 5
  givenname: Weibin
  surname: Fan
  fullname: Fan, Weibin
  organization: State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China
– sequence: 6
  givenname: Deguang
  orcidid: 0000-0002-9034-2842
  surname: Huang
  fullname: Huang, Deguang
  email: dhuang@fjirsm.ac.cn
  organization: State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China
BackLink https://www.ncbi.nlm.nih.gov/pubmed/34908092$$D View this record in MEDLINE/PubMed
BookMark eNpFkEtOwzAQhi1URB-w4QDIa4TBjpO4ZlfKo0iVumj3lR1P2kDiVLYj0TtwGThIz0SqQlnN65t_NH8fdWxtAaFLRm8Z5fLukc0eaERjPjpBPRYLQWjCZeeYR7SL-t6_UcqkSOMz1OWxpEMqox76nG9tWIMvPK5zXEFYb0uwQLQrzAoM3n3d7L5JY70KjVOh7bxDaM_7-3ZExthvMMdkctxUoajtXkq5umqL7I_HjS_sCs-hhCzkZVM7rDxWuCpKg-uPwigbztFprkoPF79xgBbPT4vxhExnL6_j0ZRkUkZkyDXwJFVGpFGaGW2oTNIMIFOaCwE6V5BoYxLB2pkROdURZQBp-3KexCLiA3R9kM1c7b2DfLlxRaXcdsnocu_o8t_RFr46wJtGV2CO6J-F_AcNL3ea
CitedBy_id crossref_primary_10_1016_j_tetlet_2022_154179
crossref_primary_10_1002_adsc_202301352
Cites_doi 10.1039/C4RA04419C
10.1039/C7OB02011B
10.1039/C7GC03719H
10.1021/ja104917t
10.1039/C8OB00349A
10.1039/D0OB01054E
10.1039/C3CC47926A
10.1002/adsc.201900717
10.1021/acs.joc.7b00619
10.1021/acs.orglett.6b01292
10.1039/c3ra40695d
10.1002/slct.201800446
10.1021/ar800214s
10.1002/asia.202000011
10.1021/ol501183z
10.1021/ar300340k
10.1021/acs.joc.5b02593
10.1039/c3ob41510d
10.1039/c1cc11603g
10.1002/asia.201403358
10.1021/ol403040g
10.1039/C6OB00977H
10.1021/acs.joc.5b00261
10.1021/acs.joc.7b01790
10.1002/slct.201802450
10.1039/C9OB00875F
10.1021/acs.joc.8b02755
10.1021/cs5005129
10.1002/adsc.201901021
10.1039/C8OB00532J
10.1039/C4CC02275K
10.1039/c2cc32009f
10.6023/cjoc202004005
10.1139/cjc-2018-0181
10.1002/anie.201608433
10.1021/acs.joc.5b00084
10.1039/C4RA14249G
10.1002/adsc.201400332
10.1002/adsc.201501007
10.1021/acs.orglett.7b02753
10.1002/slct.201900113
10.1039/C9RA01481K
10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U
10.1021/acs.orglett.5b03058
10.1039/D0OB01838D
10.1039/D1OB00120E
10.1039/c3cs35505e
10.1021/acs.joc.7b01515
10.1039/c2cs35183h
ContentType Journal Article
DBID NPM
AAYXX
CITATION
DOI 10.1039/D1OB02043A
DatabaseName PubMed
CrossRef
DatabaseTitle PubMed
CrossRef
DatabaseTitleList PubMed
CrossRef
Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1477-0539
EndPage 419
ExternalDocumentID 10_1039_D1OB02043A
34908092
Genre Journal Article
GroupedDBID ---
-DZ
-JG
-~X
0-7
0R~
123
29N
4.4
705
70~
7~J
AAEMU
AAIWI
AAJAE
AAMEH
AANOJ
AAWGC
AAXHV
AAXPP
ABASK
ABDVN
ABEMK
ABJNI
ABPDG
ABRYZ
ABXOH
ACGFS
ACIWK
ACLDK
ACNCT
ACPRK
ADMRA
ADSRN
AEFDR
AENEX
AENGV
AESAV
AETIL
AFLYV
AFOGI
AFRAH
AFRDS
AFVBQ
AGEGJ
AGKEF
AGRSR
AGSTE
AHGCF
ALMA_UNASSIGNED_HOLDINGS
ANUXI
APEMP
ASKNT
AUDPV
BLAPV
BSQNT
C6K
CS3
D0L
DU5
EBS
ECGLT
EE0
EF-
F5P
GGIMP
GNO
H13
HZ~
H~N
IDZ
J3I
M4U
N9A
NPM
O9-
OK1
P2P
R7B
R7C
RAOCF
RCNCU
RNS
RPMJG
RRA
RRC
RSCEA
SKA
SKF
SLH
TN5
TWZ
UCJ
VH6
VQA
WH7
XSW
YNT
YZZ
AAYXX
CITATION
ID FETCH-LOGICAL-c992-83be356ad7626cdbd0956ceecab377ebfae5bdd571dbdd7f0b201ee6908f54723
ISSN 1477-0520
IngestDate Fri Aug 23 03:00:51 EDT 2024
Sat Sep 28 08:24:13 EDT 2024
IsPeerReviewed true
IsScholarly true
Issue 2
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c992-83be356ad7626cdbd0956ceecab377ebfae5bdd571dbdd7f0b201ee6908f54723
ORCID 0000-0002-9034-2842
PMID 34908092
PageCount 5
ParticipantIDs crossref_primary_10_1039_D1OB02043A
pubmed_primary_34908092
PublicationCentury 2000
PublicationDate 2022-Jan-05
2022-01-05
PublicationDateYYYYMMDD 2022-01-05
PublicationDate_xml – month: 01
  year: 2022
  text: 2022-Jan-05
  day: 05
PublicationDecade 2020
PublicationPlace England
PublicationPlace_xml – name: England
PublicationTitle Organic & biomolecular chemistry
PublicationTitleAlternate Org Biomol Chem
PublicationYear 2022
References Cao (D1OB02043A/cit7f/1) 2018; 3
Fei (D1OB02043A/cit6b/1) 2013; 11
Liu (D1OB02043A/cit8h/1) 2019; 17
Pawar (D1OB02043A/cit8a/1) 2014; 50
Kong (D1OB02043A/cit5b/1) 2020; 40
Liu (D1OB02043A/cit6g/1) 2017; 82
Guo (D1OB02043A/cit2b/1) 2017; 56
Xu (D1OB02043A/cit4b/1) 2019; 32
Sun (D1OB02043A/cit7a/1) 2015; 5
Kibriya (D1OB02043A/cit12e/1) 2018; 16
Marson (D1OB02043A/cit1c/1) 2012; 41
Chen (D1OB02043A/cit2a/1) 2015; 17
Liu (D1OB02043A/cit14/1) 2015; 80
Ke (D1OB02043A/cit5a/1) 2020; 15
Borah (D1OB02043A/cit8e/1) 2015; 80
Zhu (D1OB02043A/cit7d/1) 2017; 82
Gao (D1OB02043A/cit13b/1) 2018; 16
Zhang (D1OB02043A/cit12a/1) 2012; 48
Wu (D1OB02043A/cit6d/1) 2016; 358
Zhao (D1OB02043A/cit8c/1) 2014; 16
Rao (D1OB02043A/cit8f/1) 2016; 18
Cao (D1OB02043A/cit10b/1) 2019; 9
Wen (D1OB02043A/cit6h/1) 2017; 19
Wan (D1OB02043A/cit1e/1) 2017; 15
Jin (D1OB02043A/cit11/1) 2021; 19
Meng (D1OB02043A/cit8j/1) 2020; 18
Shu (D1OB02043A/cit6j/1) 2019; 84
Tashrifi (D1OB02043A/cit6i/1) 2019; 362
Qian (D1OB02043A/cit6c/1) 2014; 356
Sun (D1OB02043A/cit7c/1) 2016; 81
Zhao (D1OB02043A/cit4a/1) 2013; 26
Ren (D1OB02043A/cit6a/1) 2011; 47
Zhao (D1OB02043A/cit12b/1) 2013; 3
Brauch (D1OB02043A/cit1d/1) 2013; 42
Liu (D1OB02043A/cit8b/1) 2014; 50
Liu (D1OB02043A/cit6e/1) 2016; 14
Li (D1OB02043A/cit8d/1) 2014; 16
Dömling (D1OB02043A/cit1a/1) 2000; 39
Yao (D1OB02043A/cit7e/1) 2018; 3
Liu (D1OB02043A/cit12d/1) 2017; 82
Xing (D1OB02043A/cit13a/1) 2014; 4
Xiao (D1OB02043A/cit2c/1) 2018; 20
Weng (D1OB02043A/cit8g/1) 2017; 82
Chen (D1OB02043A/cit10a/1) 2019; 4
Ji (D1OB02043A/cit8k/1) 2020; 18
Liu (D1OB02043A/cit6f/1) 2017; 82
Guo (D1OB02043A/cit3/1) 2013; 46
Cao (D1OB02043A/cit9/1) 2019; 97
Sun (D1OB02043A/cit7b/1) 2015; 10
Ganem (D1OB02043A/cit1b/1) 2009; 42
Li (D1OB02043A/cit12c/1) 2014; 4
Kim (D1OB02043A/cit8i/1) 2020; 132
References_xml – volume: 4
  start-page: 26783
  year: 2014
  ident: D1OB02043A/cit13a/1
  publication-title: RSC Adv.
  doi: 10.1039/C4RA04419C
  contributor:
    fullname: Xing
– volume: 15
  start-page: 9031
  year: 2017
  ident: D1OB02043A/cit1e/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/C7OB02011B
  contributor:
    fullname: Wan
– volume: 20
  start-page: 973
  year: 2018
  ident: D1OB02043A/cit2c/1
  publication-title: Green Chem.
  doi: 10.1039/C7GC03719H
  contributor:
    fullname: Xiao
– volume: 132
  start-page: 10272
  year: 2020
  ident: D1OB02043A/cit8i/1
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja104917t
  contributor:
    fullname: Kim
– volume: 16
  start-page: 2342
  year: 2018
  ident: D1OB02043A/cit13b/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/C8OB00349A
  contributor:
    fullname: Gao
– volume: 18
  start-page: 4922
  year: 2020
  ident: D1OB02043A/cit8j/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/D0OB01054E
  contributor:
    fullname: Meng
– volume: 82
  start-page: 9189
  year: 2017
  ident: D1OB02043A/cit12d/1
  publication-title: J. Org. Chem.
  contributor:
    fullname: Liu
– volume: 50
  start-page: 448
  year: 2014
  ident: D1OB02043A/cit8a/1
  publication-title: Chem. Commun.
  doi: 10.1039/C3CC47926A
  contributor:
    fullname: Pawar
– volume: 32
  start-page: 4278
  year: 2019
  ident: D1OB02043A/cit4b/1
  publication-title: Adv. Synth. Catal.
  doi: 10.1002/adsc.201900717
  contributor:
    fullname: Xu
– volume: 82
  start-page: 7159
  year: 2017
  ident: D1OB02043A/cit6f/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.7b00619
  contributor:
    fullname: Liu
– volume: 18
  start-page: 3142
  year: 2016
  ident: D1OB02043A/cit8f/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.6b01292
  contributor:
    fullname: Rao
– volume: 3
  start-page: 10272
  year: 2013
  ident: D1OB02043A/cit12b/1
  publication-title: RSC Adv.
  doi: 10.1039/c3ra40695d
  contributor:
    fullname: Zhao
– volume: 3
  start-page: 9374
  year: 2018
  ident: D1OB02043A/cit7f/1
  publication-title: ChemistrySelect
  doi: 10.1002/slct.201800446
  contributor:
    fullname: Cao
– volume: 42
  start-page: 463
  year: 2009
  ident: D1OB02043A/cit1b/1
  publication-title: Acc. Chem. Res.
  doi: 10.1021/ar800214s
  contributor:
    fullname: Ganem
– volume: 15
  start-page: 729
  year: 2020
  ident: D1OB02043A/cit5a/1
  publication-title: Chem. – Asian J.
  doi: 10.1002/asia.202000011
  contributor:
    fullname: Ke
– volume: 16
  start-page: 3082
  year: 2014
  ident: D1OB02043A/cit8c/1
  publication-title: Org. Lett.
  doi: 10.1021/ol501183z
  contributor:
    fullname: Zhao
– volume: 46
  start-page: 2427
  year: 2013
  ident: D1OB02043A/cit3/1
  publication-title: Acc. Chem. Res.
  doi: 10.1021/ar300340k
  contributor:
    fullname: Guo
– volume: 81
  start-page: 1476
  year: 2016
  ident: D1OB02043A/cit7c/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.5b02593
  contributor:
    fullname: Sun
– volume: 11
  start-page: 7092
  year: 2013
  ident: D1OB02043A/cit6b/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/c3ob41510d
  contributor:
    fullname: Fei
– volume: 47
  start-page: 6725
  year: 2011
  ident: D1OB02043A/cit6a/1
  publication-title: Chem. Commun.
  doi: 10.1039/c1cc11603g
  contributor:
    fullname: Ren
– volume: 10
  start-page: 536
  year: 2015
  ident: D1OB02043A/cit7b/1
  publication-title: Chem. – Asian J.
  doi: 10.1002/asia.201403358
  contributor:
    fullname: Sun
– volume: 16
  start-page: 66
  year: 2014
  ident: D1OB02043A/cit8d/1
  publication-title: Org. Lett.
  doi: 10.1021/ol403040g
  contributor:
    fullname: Li
– volume: 14
  start-page: 6523
  year: 2016
  ident: D1OB02043A/cit6e/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/C6OB00977H
  contributor:
    fullname: Liu
– volume: 80
  start-page: 4749
  year: 2015
  ident: D1OB02043A/cit14/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.5b00261
  contributor:
    fullname: Liu
– volume: 82
  start-page: 12059
  year: 2017
  ident: D1OB02043A/cit7d/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.7b01790
  contributor:
    fullname: Zhu
– volume: 3
  start-page: 13006
  year: 2018
  ident: D1OB02043A/cit7e/1
  publication-title: ChemistrySelect
  doi: 10.1002/slct.201802450
  contributor:
    fullname: Yao
– volume: 17
  start-page: 6153
  year: 2019
  ident: D1OB02043A/cit8h/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/C9OB00875F
  contributor:
    fullname: Liu
– volume: 26
  start-page: 10272
  year: 2013
  ident: D1OB02043A/cit4a/1
  publication-title: RSC Adv.
  doi: 10.1039/c3ra40695d
  contributor:
    fullname: Zhao
– volume: 84
  start-page: 2962
  year: 2019
  ident: D1OB02043A/cit6j/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.8b02755
  contributor:
    fullname: Shu
– volume: 4
  start-page: 1897
  year: 2014
  ident: D1OB02043A/cit12c/1
  publication-title: ACS Catal.
  doi: 10.1021/cs5005129
  contributor:
    fullname: Li
– volume: 362
  start-page: 65
  year: 2019
  ident: D1OB02043A/cit6i/1
  publication-title: Adv. Synth. Catal.
  doi: 10.1002/adsc.201901021
  contributor:
    fullname: Tashrifi
– volume: 16
  start-page: 3473
  year: 2018
  ident: D1OB02043A/cit12e/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/C8OB00532J
  contributor:
    fullname: Kibriya
– volume: 50
  start-page: 7636
  year: 2014
  ident: D1OB02043A/cit8b/1
  publication-title: Chem. Commun.
  doi: 10.1039/C4CC02275K
  contributor:
    fullname: Liu
– volume: 48
  start-page: 5928
  year: 2012
  ident: D1OB02043A/cit12a/1
  publication-title: Chem. Commun.
  doi: 10.1039/c2cc32009f
  contributor:
    fullname: Zhang
– volume: 40
  start-page: 2641
  year: 2020
  ident: D1OB02043A/cit5b/1
  publication-title: Chin. J. Org. Chem.
  doi: 10.6023/cjoc202004005
  contributor:
    fullname: Kong
– volume: 97
  start-page: 37
  year: 2019
  ident: D1OB02043A/cit9/1
  publication-title: Can. J. Org. Chem.
  doi: 10.1139/cjc-2018-0181
  contributor:
    fullname: Cao
– volume: 56
  start-page: 1289
  year: 2017
  ident: D1OB02043A/cit2b/1
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.201608433
  contributor:
    fullname: Guo
– volume: 80
  start-page: 4722
  year: 2015
  ident: D1OB02043A/cit8e/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.5b00084
  contributor:
    fullname: Borah
– volume: 82
  start-page: 7159
  year: 2017
  ident: D1OB02043A/cit6g/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.7b00619
  contributor:
    fullname: Liu
– volume: 5
  start-page: 3094
  year: 2015
  ident: D1OB02043A/cit7a/1
  publication-title: RSC Adv.
  doi: 10.1039/C4RA14249G
  contributor:
    fullname: Sun
– volume: 356
  start-page: 3119
  year: 2014
  ident: D1OB02043A/cit6c/1
  publication-title: Adv. Synth. Catal.
  doi: 10.1002/adsc.201400332
  contributor:
    fullname: Qian
– volume: 358
  start-page: 336
  year: 2016
  ident: D1OB02043A/cit6d/1
  publication-title: Adv. Synth. Catal.
  doi: 10.1002/adsc.201501007
  contributor:
    fullname: Wu
– volume: 19
  start-page: 5798
  year: 2017
  ident: D1OB02043A/cit6h/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.7b02753
  contributor:
    fullname: Wen
– volume: 4
  start-page: 2404
  year: 2019
  ident: D1OB02043A/cit10a/1
  publication-title: ChemistrySelect
  doi: 10.1002/slct.201900113
  contributor:
    fullname: Chen
– volume: 9
  start-page: 10340
  year: 2019
  ident: D1OB02043A/cit10b/1
  publication-title: RSC Adv.
  doi: 10.1039/C9RA01481K
  contributor:
    fullname: Cao
– volume: 39
  start-page: 3168
  year: 2000
  ident: D1OB02043A/cit1a/1
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U
  contributor:
    fullname: Dömling
– volume: 17
  start-page: 5870
  year: 2015
  ident: D1OB02043A/cit2a/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.5b03058
  contributor:
    fullname: Chen
– volume: 18
  start-page: 9100
  year: 2020
  ident: D1OB02043A/cit8k/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/D0OB01838D
  contributor:
    fullname: Ji
– volume: 19
  start-page: 4076
  year: 2021
  ident: D1OB02043A/cit11/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/D1OB00120E
  contributor:
    fullname: Jin
– volume: 42
  start-page: 4948
  year: 2013
  ident: D1OB02043A/cit1d/1
  publication-title: Chem. Soc. Rev.
  doi: 10.1039/c3cs35505e
  contributor:
    fullname: Brauch
– volume: 82
  start-page: 9047
  year: 2017
  ident: D1OB02043A/cit8g/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.7b01515
  contributor:
    fullname: Weng
– volume: 41
  start-page: 7712
  year: 2012
  ident: D1OB02043A/cit1c/1
  publication-title: Chem. Soc. Rev.
  doi: 10.1039/c2cs35183h
  contributor:
    fullname: Marson
SSID ssj0019764
Score 2.398086
Snippet A three starting material four component reaction (3SM-4CR) is developed for the synthesis of α,β-unsaturated ketones and β-amino ketones in good yields. The...
SourceID crossref
pubmed
SourceType Aggregation Database
Index Database
StartPage 415
Title Synthesis of methylene-bridged α,β-unsaturated ketones: α-C sp 3 -H methylenation of aromatic ketones using Selectfluor as a mild oxidant
URI https://www.ncbi.nlm.nih.gov/pubmed/34908092
Volume 20
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3NjtMwELZK9wAXxD_LnyzBnoIhjeMk5dYNRQXxc9giLafKsR2IWNKybSTKiSfgwpPAQ3Dch-BJGNtxklIOC1IVRY7HSjOfZsbj-UHonhxKGamAEiVYQELOGOEyZsSXfh5RlQgptEP_xcto8jp8dsgOe72fnailapU9EJ__mlfyP1yFMeCrzpL9B842i8IA3AN_4QochuupeHywLsF-q0uK6F7Qa9AhitgkLOntpeO9fZBUqbkJSFUudRlPro3M92plqvTTUT2NpN5y4VHPRT_QSbNiY1Xy47mt8FpTe5XxNByYXjr5UaUDMpce9z4UR9KbfyokLzdc_zbxUxi46bx_15rXE67t3JYf-03VCRoqKnOW8q74WLQTKwu58u26ajHqqJ1irv0aQWD8GqwjisM4JjpKx2qq7pgtf-Tkdz2j6GyjrTAObaJorddDK5q3VIZPdcXVx4NX-yZPuCm62tbl_kNfNlGM5vyeDmct7Rm0E4DAS_poZzSePn3enGeB0WfiG9x_coVy6fBhS71hGm1scoyxM72Azte7FDyykLuIeqq8hM6mjkuX0dcGenie4y3o4ZPv909-dAGHa8g8gkckxcsFpvjXl28TvAEyvZgDmaPABmS4AzLMl5hjDTJcg-wKmj4ZT9MJqVt7EKHDnROaKcoikAqwnxYyk7ocJphrgmc0jlWWc8UyKVk8gGcyzv0M7FSloqGf5CyMA3oV9Ut4hesIa3s_EBx-IgZrM8lkNkhEIPIgizgdsF10133U2cIWcJltM24XXbPfu5lD9Ym4PwxunIr-JjrXYvgW6q-OK3UbrNVVdqeGwm8qbpjz
link.rule.ids 315,783,787,27938,27939
linkProvider Royal Society of Chemistry
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=Synthesis+of+methylene-bridged+%CE%B1%2C%CE%B2-unsaturated+ketones%3A+%CE%B1-C+sp+3+%E2%80%93H+methylenation+of+aromatic+ketones+using+Selectfluor+as+a+mild+oxidant&rft.jtitle=Organic+%26+biomolecular+chemistry&rft.au=Zhang%2C+Yuan&rft.au=Liu%2C+Zhiqi&rft.au=Zhu%2C+Tingyu&rft.au=Huang%2C+Ying&rft.date=2022-01-05&rft.issn=1477-0520&rft.eissn=1477-0539&rft.volume=20&rft.issue=2&rft.spage=415&rft.epage=419&rft_id=info:doi/10.1039%2FD1OB02043A&rft.externalDBID=n%2Fa&rft.externalDocID=10_1039_D1OB02043A
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1477-0520&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1477-0520&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1477-0520&client=summon