Pd-0-Catalyzed Intramolecular alpha-Arylation of Sulfones: Domino Reactions in the Synthesis of Functionalized Tetrahydroisoquinolines

A new strategy for the synthesis of tetrahydroisoquinolines based on the Pd-0-catalyzed intramolecular -arylation of sulfones is reported. The combination of this Pd-catalyzed reaction with intermolecular Michael and aza-Michael reactions allows the development of two- and three-step domino processe...

Full description

Saved in:
Bibliographic Details
Published inChemistry : a European journal Vol. 21; no. 12; pp. 4580 - 4584
Main Authors Sole, Daniel, Perez-Janer, Ferran, Mancuso, Raffaella
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 16.03.2015
Subjects
Online AccessGet full text

Cover

Loading…
Abstract A new strategy for the synthesis of tetrahydroisoquinolines based on the Pd-0-catalyzed intramolecular -arylation of sulfones is reported. The combination of this Pd-catalyzed reaction with intermolecular Michael and aza-Michael reactions allows the development of two- and three-step domino processes to synthesize diversely functionalized scaffolds from readily available starting materials.
AbstractList Abstract A new strategy for the synthesis of tetrahydroisoquinolines based on the Pd 0 ‐catalyzed intramolecular α‐arylation of sulfones is reported. The combination of this Pd‐catalyzed reaction with intermolecular Michael and aza‐Michael reactions allows the development of two‐ and three‐step domino processes to synthesize diversely functionalized scaffolds from readily available starting materials.
A new strategy for the synthesis of tetrahydroisoquinolines based on the Pd-0-catalyzed intramolecular -arylation of sulfones is reported. The combination of this Pd-catalyzed reaction with intermolecular Michael and aza-Michael reactions allows the development of two- and three-step domino processes to synthesize diversely functionalized scaffolds from readily available starting materials.
Author Sole, Daniel
Perez-Janer, Ferran
Mancuso, Raffaella
Author_xml – sequence: 1
  givenname: Daniel
  surname: Sole
  fullname: Sole, Daniel
  email: dsole@ub.edu
  organization: Univ Barcelona, Fac Farm, Lab Quim Organ, E-08028 Barcelona, Spain
– sequence: 2
  givenname: Ferran
  surname: Perez-Janer
  fullname: Perez-Janer, Ferran
  organization: Univ Barcelona, Fac Farm, Lab Quim Organ, E-08028 Barcelona, Spain
– sequence: 3
  givenname: Raffaella
  surname: Mancuso
  fullname: Mancuso, Raffaella
  organization: Univ Barcelona, Fac Farm, Lab Quim Organ, E-08028 Barcelona, Spain
BookMark eNqNkEtP3DAURi00CIbHtmvvqwx-xHbc3ShlAGmkIh7ryONca1x5bBonQuEH8LubQMW6d_Mt7j2frs4ZWsQUAaFvlKwoIezK7uGwYoSWRHIijtCSCkYLrqRYoCXRpSqk4PoUneX8mxCiJecn6JQJqRSp-BK937cFKWrTmzC-QYvvYt-ZQwpgh2A6bMLL3hTrbgym9yni5PDjENz0Q_6Bf6aDjwk_gLHzMmMfcb8H_DjGKbLP8_lmiB9bE_zc_wRT_35su-Rz-jNMfPBT2QU6diZkuPyX5-h5c_1U3xbbXzd39XpbWCp1XyhJOXXVDiTY1nLFHTDaSut4q5jTpaFMV5px4KKlwqhy53RVMQ2iLG1bcn6OVp-9tks5d-Cal84fTDc2lDSz0GYW2nwJnYDqE3iFXXLZeogWvqDJKBdESTIPrWrff2iq0xD7Cf3-_yj_C1cEjUU
CitedBy_id crossref_primary_10_1002_chin_201532174
crossref_primary_10_3390_catal8100458
crossref_primary_10_1021_acs_joc_8b00287
crossref_primary_10_1002_ajoc_202200440
crossref_primary_10_1002_anie_201602020
crossref_primary_10_1002_ange_201602020
crossref_primary_10_1021_acs_joc_6b00341
crossref_primary_10_1002_ejoc_201601300
crossref_primary_10_1016_j_tet_2019_02_041
crossref_primary_10_3390_molecules24193551
crossref_primary_10_1039_D3NJ04668K
crossref_primary_10_1055_a_2282_7702
crossref_primary_10_1002_chem_201902104
crossref_primary_10_1021_acscatal_6b00027
Cites_doi 10.1016/j.tet.2009.01.030
10.1002/adsc.200404148
10.1016/j.tetlet.2009.12.035
10.1021/jm701623q
10.1002/ejoc.201001621
10.1016/j.bmc.2004.11.039
10.1021/ar400104j
10.1016/j.bmcl.2010.04.104
10.1021/ja029114w
10.1021/ol501389k
10.1021/jo101054j
10.1039/b911852g
10.1055/s-0030-1260934
10.1080/10426500590910657
10.1021/co200181x
10.1039/c2ob25854d
10.1002/anie.200903424
10.1021/ol400472v
10.1002/anie.201307172
10.1021/ja4009776
10.1021/jo034299q
10.1002/adsc.201300678
10.1016/j.tet.2012.06.106
10.1039/b509523a
10.1021/jo301924e
10.1080/10426507.2012.740703
10.1039/b909701e
10.1021/cr9000836
10.1039/b804167a
10.1039/c0ob00835d
10.3390/molecules16108515
10.1016/j.tetlet.2004.02.086
10.1002/anie.200906340
10.1021/jo8020715
10.1021/np2009016
10.1021/ar0201106
10.1021/jo800034m
10.1002/anie.201307019
10.1002/chem.201102811
10.1039/c1ob05087g
10.1016/B978-0-08-096805-6.00012-7
10.1039/B509523A
10.1016/S0040-4039(02)00321-0
10.1002/ejoc.201200572
10.1002/ange.200903424
10.1002/1615-4169(200107)343:5<439::AID-ADSC439>3.0.CO;2-G
10.1021/np50076a023
10.1002/ange.200906340
10.1021/ol005973i
10.2174/13895575110091235
10.1021/cr950027e
ContentType Journal Article
DBID 1KM
1KN
BLEPL
DTL
GVOUP
AAYXX
CITATION
DOI 10.1002/chem.201406305
DatabaseName Index Chemicus
Current Chemical Reactions
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 2015
CrossRef
DatabaseTitle Web of Science
CrossRef
DatabaseTitleList CrossRef
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 1521-3765
EndPage 4584
ExternalDocumentID 10_1002_chem_201406305
000350760000018
GrantInformation_xml – fundername: Spanish MINECO-FEDER
  grantid: CTQ2012-31391
GroupedDBID ---
-DZ
-~X
.3N
.GA
05W
0R~
10A
1KM
1KN
1L6
1OB
1OC
1ZS
29B
33P
3SF
3WU
4.4
4ZD
50Y
50Z
51W
51X
52M
52N
52O
52P
52S
52T
52U
52W
52X
53G
5GY
5VS
66C
6J9
702
77Q
7PT
8-0
8-1
8-3
8-4
8-5
8UM
930
A03
AAESR
AAEVG
AAHHS
AANLZ
AAONW
AASGY
AAXRX
AAZKR
ABCQN
ABCUV
ABDBF
ABIJN
ABJNI
ABLJU
ABPVW
ACAHQ
ACBWZ
ACCFJ
ACCZN
ACGFS
ACIWK
ACNCT
ACPOU
ACXBN
ACXQS
ADBBV
ADEOM
ADIZJ
ADKYN
ADMGS
ADOZA
ADXAS
ADZMN
ADZOD
AEEZP
AEGXH
AEIGN
AEIMD
AEQDE
AEUQT
AEUYR
AFBPY
AFFPM
AFGKR
AFPWT
AFRAH
AFZJQ
AHBTC
AHMBA
AITYG
AIURR
AIWBW
AJBDE
AJXKR
ALAGY
ALMA_UNASSIGNED_HOLDINGS
AMBMR
AMYDB
ATUGU
AUFTA
AZBYB
AZVAB
BAFTC
BDRZF
BFHJK
BHBCM
BLEPL
BMNLL
BMXJE
BNHUX
BROTX
BRXPI
BY8
CS3
D-E
D-F
DCZOG
DPXWK
DR2
DRFUL
DRSTM
DTL
EBD
EBS
EJD
F00
F01
F04
F5P
G-S
G.N
GNP
GODZA
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
H.T
H.X
HBH
HGLYW
HHY
HHZ
HZ~
IX1
J0M
JPC
KQQ
LATKE
LAW
LC2
LC3
LEEKS
LH4
LITHE
LOXES
LP6
LP7
LUTES
LW6
LYRES
MEWTI
MK4
MRFUL
MRSTM
MSFUL
MSSTM
MXFUL
MXSTM
N04
N05
N9A
NF~
NNB
O66
O9-
OIG
P2W
P2X
P4D
PQQKQ
Q.N
Q11
QB0
QRW
R.K
RGC
RNS
ROL
RWI
RX1
RYL
SUPJJ
TN5
TWZ
UB1
UPT
V2E
V8K
W8V
W99
WBFHL
WBKPD
WH7
WIB
WIH
WIK
WJL
WOHZO
WQJ
WRC
WXSBR
WYISQ
XG1
XPP
XV2
YZZ
ZZTAW
~IA
~WT
AAYXX
CITATION
ID FETCH-LOGICAL-c169t-76131f8be6ecdc373fe21d6cf3d72f94a1298923e35d15a74bf98829e544cd433
ISICitedReferencesCount 14
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000350760000018
ISSN 0947-6539
IngestDate Fri Aug 23 03:32:06 EDT 2024
Fri Oct 11 20:31:39 EDT 2024
Wed Sep 18 05:02:53 EDT 2024
IsPeerReviewed true
IsScholarly true
Issue 12
Keywords AZA-MICHAEL ADDITION
ISOQUINOLINE ALKALOIDS
arylation
sulfones
domino reactions
CYCLIZATION REACTIONS
nitrogen heterocycles
ARYL HALIDES
ESTERS
palladium
ENOLATE ARYLATION
DERIVATIVES
TETHERED VINYL HALIDES
PD-CATALYZED REACTIONS
CATALYZED DIRECT ARYLATION
Language English
LinkModel OpenURL
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c169t-76131f8be6ecdc373fe21d6cf3d72f94a1298923e35d15a74bf98829e544cd433
PMID 25677083
PageCount 5
ParticipantIDs crossref_primary_10_1002_chem_201406305
webofscience_primary_000350760000018
webofscience_primary_000350760000018CitationCount
PublicationCentury 2000
PublicationDate 2015-03-16
PublicationDateYYYYMMDD 2015-03-16
PublicationDate_xml – month: 03
  year: 2015
  text: 2015-03-16
  day: 16
PublicationDecade 2010
PublicationPlace WEINHEIM
PublicationPlace_xml – name: WEINHEIM
PublicationTitle Chemistry : a European journal
PublicationTitleAbbrev CHEM-EUR J
PublicationYear 2015
Publisher Wiley
Publisher_xml – name: Wiley
References Kashin, AN (WOS:000174978100013) 2002; 43
Rene, O (WOS:000340808000013) 2014; 16
Yang, F (WOS:000303220500041) 2012; 75
Sole, D (WOS:000254060400066) 2008; 73
Cao, SG (WOS:000226967900006) 2005; 13
Alford, PE (WOS:000307480800012) 2011; 23
Sole, D (WOS:000281585600026) 2010; 75
Nielsen, M (WOS:000276780500006) 2010; 49
Jia, TZ (WOS:000316244200003) 2013; 135
Sole, D (WOS:000261316100022) 2008; 73
Zheng, B (WOS:000317327900069) 2013; 15
Sole, D (WOS:000180842200039) 2003; 125
Zang, Q (WOS:000301310600011) 2012; 14
Chen, K (WOS:000306854600020) 2012; 10
Priebbenow, DL (WOS:000288130000003) 2011; 2011
Garuti, L. (000350760000018.11) 2005; 12
Johansson, CCC (WOS:000274424000003) 2010; 49
Sole, D (WOS:000220554500028) 2004; 45
Bachmann, DG (WOS:000329021600026) 2013; 355
Sole, D (WOS:000170369800007) 2001; 343
Alonso, DA (WOS:000228669300002) 2005; 180
Niwa, T (WOS:000263945800005) 2009; 65
Culkin, DA (WOS:000182343300002) 2003; 36
Sole, D (WOS:000330204400017) 2014; 47
Tietze, LF (WOS:A1996TT87100006) 1996; 96
PRINSEP, MR (WOS:A1991GF52600024) 1991; 54
Xie, Y.-X. (000350760000018.50) 2014
Sasikumar, TK (WOS:000278208200039) 2010; 20
Siengalewicz, P (WOS:000261170900008) 2008; 37
Sole, D (WOS:000225985800014) 2004; 346
Sole, D (WOS:000311073000033) 2012; 77
Sole, D (WOS:000088346400012) 2000; 2
Okuro, K. (000350760000018.22) 2012; 25
Reddy, AGK (WOS:000292596600025) 2011
Jia, TZ (WOS:000328714900038) 2014; 53
Souto, AL (WOS:000296973000027) 2011; 16
Nielsen, M. (000350760000018.20) 2010; 122
Johansson, C. C. C. (000350760000018.16) 2010; 122
Reddy, AGK (WOS:000308051600038) 2012; 68
Sabatini, S (WOS:000257721600027) 2008; 51
Stout, E. P. (000350760000018.48) 2012
Nambo, M (WOS:000330983300016) 2014; 53
Simpkins, N. S. (000350760000018.32) 1993
Zhou, G (WOS:000274710200014) 2010; 51
Bhadra, K (WOS:000286093500004) 2010; 10
Bellina, F (WOS:000274705900015) 2010; 110
Sole, D (WOS:000268975300004) 2009; 7
Sole, D (WOS:000304347600031) 2012; 18
Sole, D (WOS:000291218900019) 2011; 9
Alba, ANR (WOS:000278046100012) 2010; 39
Gautam, N (WOS:000322091600017) 2013; 188
Priebbenow, DL (WOS:000287368800031) 2011; 9
Sole, D (WOS:000184060600042) 2003; 68
Bentley, KW (WOS:000237971500006) 2006; 23
e_1_2_4_40_2
e_1_2_4_61_2
e_1_2_4_44_2
e_1_2_4_21_2
e_1_2_4_42_2
e_1_2_4_23_2
e_1_2_4_48_2
Okuro K. (e_1_2_4_63_2) 2012; 25
e_1_2_4_25_2
e_1_2_4_46_2
e_1_2_4_27_2
e_1_2_4_29_2
e_1_2_4_1_2
e_1_2_4_3_2
e_1_2_4_5_3
e_1_2_4_5_2
e_1_2_4_50_2
e_1_2_4_9_2
e_1_2_4_31_2
e_1_2_4_54_2
Reddy A. G. K. (e_1_2_4_53_2) 2011
e_1_2_4_10_2
e_1_2_4_33_2
e_1_2_4_52_2
e_1_2_4_12_2
e_1_2_4_35_2
e_1_2_4_58_2
e_1_2_4_14_2
e_1_2_4_37_2
e_1_2_4_56_2
e_1_2_4_39_2
e_1_2_4_16_2
e_1_2_4_18_2
Simpkins N. S. (e_1_2_4_2_2) 1993
e_1_2_4_62_2
e_1_2_4_20_2
e_1_2_4_43_2
e_1_2_4_22_2
e_1_2_4_41_2
e_1_2_4_64_2
e_1_2_4_24_2
e_1_2_4_47_2
e_1_2_4_26_2
e_1_2_4_45_2
e_1_2_4_28_2
e_1_2_4_49_2
Garuti L. (e_1_2_4_7_2) 2005; 12
e_1_2_4_4_2
e_1_2_4_6_2
Xie Y.‐X. (e_1_2_4_60_2) 2014
e_1_2_4_8_2
e_1_2_4_51_2
e_1_2_4_30_2
e_1_2_4_55_2
e_1_2_4_11_2
e_1_2_4_32_2
e_1_2_4_13_2
e_1_2_4_34_2
e_1_2_4_59_2
e_1_2_4_15_2
e_1_2_4_36_2
e_1_2_4_57_2
e_1_2_4_17_2
e_1_2_4_38_2
e_1_2_4_19_2
e_1_2_4_19_3
References_xml – volume: 65
  start-page: 1971
  year: 2009
  ident: WOS:000263945800005
  article-title: Palladium-catalyzed benzylic direct arylation of benzyl sulfones with aryl halides
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2009.01.030
  contributor:
    fullname: Niwa, T
– volume: 346
  start-page: 1646
  year: 2004
  ident: WOS:000225985800014
  article-title: Palladium-catalyzed intramolecular coupling of amino-tethered vinyl halides with ketones, esters, and nitriles using potassium phenoxide as the base
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.200404148
  contributor:
    fullname: Sole, D
– volume: 51
  start-page: 939
  year: 2010
  ident: WOS:000274710200014
  article-title: Palladium-catalyzed Negishi alpha-arylation of alkylsulfones
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2009.12.035
  contributor:
    fullname: Zhou, G
– volume: 51
  start-page: 4321
  year: 2008
  ident: WOS:000257721600027
  article-title: From phenothiazine to 3-phenyl-1,4-benzothiazine derivatives as inhibitors of the Staphylococcus aureus NorA multidrug efflux pump
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm701623q
  contributor:
    fullname: Sabatini, S
– volume: 2011
  start-page: 1632
  year: 2011
  ident: WOS:000288130000003
  article-title: A One-Pot, Three-Component Approach to Functionalised Tetrahydroisoquinolines Using Domino Heck-aza-Michael Reactions
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1002/ejoc.201001621
  contributor:
    fullname: Priebbenow, DL
– volume: 13
  start-page: 999
  year: 2005
  ident: WOS:000226967900006
  article-title: Halenaquinone and xestoquinone derivatives, inhibitors of Cdc25B phosphatase from a Xestospongia sp.
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  doi: 10.1016/j.bmc.2004.11.039
  contributor:
    fullname: Cao, SG
– volume: 122
  start-page: 686
  year: 2010
  ident: 000350760000018.16
  publication-title: Angew. Chem.
  contributor:
    fullname: Johansson, C. C. C.
– volume: 47
  start-page: 168
  year: 2014
  ident: WOS:000330204400017
  article-title: Controlling the Ambiphilic Nature of sigma-Arylpalladium Intermediates in Intramolecular Cyclization Reactions
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar400104j
  contributor:
    fullname: Sole, D
– volume: 20
  start-page: 3632
  year: 2010
  ident: WOS:000278208200039
  article-title: Tricyclic sulfones as orally active gamma-secretase inhibitors: Synthesis and structure-activity relationship studies
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2010.04.104
  contributor:
    fullname: Sasikumar, TK
– year: 1993
  ident: 000350760000018.32
  publication-title: Sulphones in Organic Synthesis
  contributor:
    fullname: Simpkins, N. S.
– volume: 125
  start-page: 1587
  year: 2003
  ident: WOS:000180842200039
  article-title: Intramolecular Pd-mediated processes of amino-tethered aryl halides and ketones: Insight into the ketone alpha-arylation and carbonyl-addition dichotomy. A new class of four-membered azapalladacycles
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja029114w
  contributor:
    fullname: Sole, D
– volume: 16
  start-page: 3468
  year: 2014
  ident: WOS:000340808000013
  article-title: Palladium-Catalyzed alpha-Arylation of Sultams with Aryl and Heteroaryl Iodides
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol501389k
  contributor:
    fullname: Rene, O
– volume: 75
  start-page: 6267
  year: 2010
  ident: WOS:000281585600026
  article-title: Selective Synthesis of Either Isoindole- or Isoindoline-1-carboxylic Acid Esters by Pd(0)-Catalyzed Enolate Arylation
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo101054j
  contributor:
    fullname: Sole, D
– volume: 39
  start-page: 2018
  year: 2010
  ident: WOS:000278046100012
  article-title: Sulfones: new reagents in organocatalysis
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/b911852g
  contributor:
    fullname: Alba, ANR
– start-page: 1756
  year: 2011
  ident: WOS:000292596600025
  article-title: Palladium-Mediated Intramolecular Buchwald-Hartwig alpha-Arylation of beta-Amino Esters: Synthesis of Functionalized Tetrahydroisoquinolines
  publication-title: SYNLETT
  doi: 10.1055/s-0030-1260934
  contributor:
    fullname: Reddy, AGK
– volume: 180
  start-page: 1119
  year: 2005
  ident: WOS:000228669300002
  article-title: Synthetic applications of pi-electron-deficient sulfones
  publication-title: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  doi: 10.1080/10426500590910657
  contributor:
    fullname: Alonso, DA
– volume: 14
  start-page: 211
  year: 2012
  ident: WOS:000301310600011
  article-title: Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy
  publication-title: ACS COMBINATORIAL SCIENCE
  doi: 10.1021/co200181x
  contributor:
    fullname: Zang, Q
– volume: 25
  start-page: 31
  year: 2012
  ident: 000350760000018.22
  publication-title: Synlett
  contributor:
    fullname: Okuro, K.
– volume: 10
  start-page: 6600
  year: 2012
  ident: WOS:000306854600020
  article-title: A tandem Heck-aza-Michael addition protocol for the one-pot synthesis of isoindolines from unprotected amines
  publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY
  doi: 10.1039/c2ob25854d
  contributor:
    fullname: Chen, K
– volume: 49
  start-page: 676
  year: 2010
  ident: WOS:000274424000003
  article-title: Metal-Catalyzed alpha-Arylation of Carbonyl and Related Molecules: Novel Trends in C-C Bond Formation by C-H Bond Functionalization
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200903424
  contributor:
    fullname: Johansson, CCC
– volume: 15
  start-page: 1690
  year: 2013
  ident: WOS:000317327900069
  article-title: Palladium-Catalyzed Direct alpha-Arylation of Methyl Sulfones with Aryl Bromides
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol400472v
  contributor:
    fullname: Zheng, B
– volume: 12
  start-page: 167
  year: 2005
  ident: 000350760000018.11
  publication-title: Curr. Med. Chem.
  contributor:
    fullname: Garuti, L.
– volume: 54
  start-page: 1068
  year: 1991
  ident: WOS:A1991GF52600024
  article-title: NEW CYTOTOXIC BETA-CARBOLINE ALKALOIDS FROM THE MARINE BRYOZOAN, CRIBRICELLINA-CRIBRARIA
  publication-title: JOURNAL OF NATURAL PRODUCTS
  contributor:
    fullname: PRINSEP, MR
– volume: 53
  start-page: 260
  year: 2014
  ident: WOS:000328714900038
  article-title: Diaryl Sulfoxides from Aryl Benzyl Sulfoxides: A Single PalladiumCatalyzed Triple Relay Process
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201307172
  contributor:
    fullname: Jia, TZ
– volume: 43
  start-page: 2539
  year: 2002
  ident: WOS:000174978100013
  article-title: Palladium-catalyzed arylation of sulfonyl CH-acids
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: Kashin, AN
– volume: 135
  start-page: 3740
  year: 2013
  ident: WOS:000316244200003
  article-title: Palladium-Catalyzed Direct Arylation of Methyl Sulfoxides with Aryl Halides
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja4009776
  contributor:
    fullname: Jia, TZ
– volume: 68
  start-page: 5746
  year: 2003
  ident: WOS:000184060600042
  article-title: Nitrogen heterocycles by palladium-catalyzed cyclization of amino-tethered vinyl halides and ketone enolates
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo034299q
  contributor:
    fullname: Sole, D
– volume: 2
  start-page: 2225
  year: 2000
  ident: WOS:000088346400012
  article-title: Palladium-catalyzed intramolecular coupling of vinyl halides and ketone enolates, synthesis of bridged azabicyclic compounds
  publication-title: ORGANIC LETTERS
  contributor:
    fullname: Sole, D
– start-page: 203
  year: 2014
  ident: 000350760000018.50
  publication-title: Synthesis
  contributor:
    fullname: Xie, Y.-X.
– volume: 355
  start-page: 3703
  year: 2013
  ident: WOS:000329021600026
  article-title: Stereoselective Heck Reactions with Vinyl Sulfoxides, Sulfides and Sulfones
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.201300678
  contributor:
    fullname: Bachmann, DG
– volume: 68
  start-page: 8003
  year: 2012
  ident: WOS:000308051600038
  article-title: A simple efficient sequential one-pot intermolecular aza-Michael addition and intramolecular Buchwald-Hartwig alpha-arylation of amines: synthesis of functionalized tetrahydroisoquinolines
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2012.06.106
  contributor:
    fullname: Reddy, AGK
– volume: 23
  start-page: 444
  year: 2006
  ident: WOS:000237971500006
  article-title: beta-Phenylethylamines and the isoquinoline alkaloids
  publication-title: NATURAL PRODUCT REPORTS
  doi: 10.1039/b509523a
  contributor:
    fullname: Bentley, KW
– volume: 77
  start-page: 10272
  year: 2012
  ident: WOS:000311073000033
  article-title: Intramolecular Pd(0)-Catalyzed Reactions of (2-lodoanilino)-aldehydes: A Joint Experimental-Computational Study
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo301924e
  contributor:
    fullname: Sole, D
– start-page: 5131
  year: 2012
  ident: 000350760000018.48
  publication-title: Eur. J. Org. Chem.
  contributor:
    fullname: Stout, E. P.
– volume: 188
  start-page: 1127
  year: 2013
  ident: WOS:000322091600017
  article-title: An Efficient Synthesis and Antimicrobial Studies of Bioactive 4H-1,4-Benzothiazine and Their Sulfone Derivatives
  publication-title: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  doi: 10.1080/10426507.2012.740703
  contributor:
    fullname: Gautam, N
– volume: 343
  start-page: 439
  year: 2001
  ident: WOS:000170369800007
  article-title: Palladium-catalyzed intramolecular coupling of aryl halides and ketone enolates: Synthesis of hexahydro-2,6-methano-1-benzazocines
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  contributor:
    fullname: Sole, D
– volume: 96
  start-page: 115
  year: 1996
  ident: WOS:A1996TT87100006
  article-title: Domino reactions in organic synthesis
  publication-title: CHEMICAL REVIEWS
  contributor:
    fullname: Tietze, LF
– volume: 7
  start-page: 3382
  year: 2009
  ident: WOS:000268975300004
  article-title: Palladium-catalysed synthesis of 1-isoindolecarboxylic acid esters and sequential Diels-Alder reactions: access to bridged- and fused-ring heterocycles
  publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY
  doi: 10.1039/b909701e
  contributor:
    fullname: Sole, D
– volume: 110
  start-page: 1082
  year: 2010
  ident: WOS:000274705900015
  article-title: Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp(3)-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr9000836
  contributor:
    fullname: Bellina, F
– volume: 37
  start-page: 2676
  year: 2008
  ident: WOS:000261170900008
  article-title: Recent progress in the total synthesis of naphthyridinomycin and lemonomycin tetrahydroisoquinoline antitumor antibiotics (TAAs)
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/b804167a
  contributor:
    fullname: Siengalewicz, P
– volume: 122
  start-page: 2726
  year: 2010
  ident: 000350760000018.20
  publication-title: Angew. Chem.
  contributor:
    fullname: Nielsen, M.
– volume: 9
  start-page: 1508
  year: 2011
  ident: WOS:000287368800031
  article-title: A general approach to N-heterocyclic scaffolds using domino Heck-aza-Michael reactions
  publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY
  doi: 10.1039/c0ob00835d
  contributor:
    fullname: Priebbenow, DL
– volume: 10
  start-page: 1235
  year: 2010
  ident: WOS:000286093500004
  article-title: Isoquinoline Alkaloids and their Binding with DNA: Calorimetry and Thermal Analysis Applications
  publication-title: MINI-REVIEWS IN MEDICINAL CHEMISTRY
  contributor:
    fullname: Bhadra, K
– volume: 16
  start-page: 8515
  year: 2011
  ident: WOS:000296973000027
  article-title: Anti-Inflammatory Activity of Alkaloids: An Update from 2000 to 2010
  publication-title: MOLECULES
  doi: 10.3390/molecules16108515
  contributor:
    fullname: Souto, AL
– volume: 45
  start-page: 3131
  year: 2004
  ident: WOS:000220554500028
  article-title: Palladium-catalysed intramolecular coupling of vinyl or aryl halides and beta,gamma-unsaturated nitronates
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2004.02.086
  contributor:
    fullname: Sole, D
– volume: 49
  start-page: 2668
  year: 2010
  ident: WOS:000276780500006
  article-title: Asymmetric Organocatalysis with Sulfones
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200906340
  contributor:
    fullname: Nielsen, M
– volume: 73
  start-page: 9372
  year: 2008
  ident: WOS:000261316100022
  article-title: Intramolecular Pd(0)-Catalyzed Reactions of beta-(2-Iodoanilino) Carboxamides: Enolate Arylation and Nucleophilic Substitution at the Carboxamide Group
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo8020715
  contributor:
    fullname: Sole, D
– volume: 75
  start-page: 774
  year: 2012
  ident: WOS:000303220500041
  article-title: Antimicrobial Metabolites from the Paracel Islands Sponge Agelas mauritiana
  publication-title: JOURNAL OF NATURAL PRODUCTS
  doi: 10.1021/np2009016
  contributor:
    fullname: Yang, F
– volume: 36
  start-page: 234
  year: 2003
  ident: WOS:000182343300002
  article-title: Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar0201106
  contributor:
    fullname: Culkin, DA
– volume: 73
  start-page: 2476
  year: 2008
  ident: WOS:000254060400066
  article-title: Synthesis of indole-3-carboxylic acid derivatives by Pd(0)-catalyzed intramolecular alpha-arylation of beta-(2-iodoanilino) esters
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo800034m
  contributor:
    fullname: Sole, D
– volume: 53
  start-page: 742
  year: 2014
  ident: WOS:000330983300016
  article-title: Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201307019
  contributor:
    fullname: Nambo, M
– volume: 18
  start-page: 6950
  year: 2012
  ident: WOS:000304347600031
  article-title: Control over the Chemoselectivity of Pd-Catalyzed Cyclization Reactions of (2-Iodoanilino)carbonyl Compounds
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  doi: 10.1002/chem.201102811
  contributor:
    fullname: Sole, D
– volume: 9
  start-page: 4535
  year: 2011
  ident: WOS:000291218900019
  article-title: Intramolecular palladium-catalysed enolate arylation of 2-and 3-iodoindole derivatives for the synthesis of beta-carbolines, gamma-carbolines, and pyrrolo[3,4-b]indoles
  publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY
  doi: 10.1039/c1ob05087g
  contributor:
    fullname: Sole, D
– volume: 23
  start-page: 329
  year: 2011
  ident: WOS:000307480800012
  article-title: Six-Membered Ring Systems: Pyridines and Benzo Derivatives
  publication-title: PROGRESS IN HETEROCYCLIC CHEMISTRY, VOL 23
  doi: 10.1016/B978-0-08-096805-6.00012-7
  contributor:
    fullname: Alford, PE
– ident: e_1_2_4_30_2
– ident: e_1_2_4_47_2
  doi: 10.1039/B509523A
– ident: e_1_2_4_8_2
  doi: 10.1021/jm701623q
– ident: e_1_2_4_32_2
  doi: 10.1021/jo034299q
– ident: e_1_2_4_5_2
  doi: 10.1002/anie.200906340
– ident: e_1_2_4_52_2
– ident: e_1_2_4_54_2
  doi: 10.1016/j.tet.2012.06.106
– ident: e_1_2_4_44_2
  doi: 10.1021/jo301924e
– ident: e_1_2_4_27_2
  doi: 10.1021/ja4009776
– start-page: 1756
  year: 2011
  ident: e_1_2_4_53_2
  publication-title: Synlett
  contributor:
    fullname: Reddy A. G. K.
– ident: e_1_2_4_21_2
  doi: 10.1016/S0040-4039(02)00321-0
– ident: e_1_2_4_25_2
  doi: 10.1002/anie.201307019
– ident: e_1_2_4_28_2
  doi: 10.1002/anie.201307172
– ident: e_1_2_4_14_2
  doi: 10.1021/np2009016
– ident: e_1_2_4_46_2
– ident: e_1_2_4_45_2
  doi: 10.1021/ar400104j
– ident: e_1_2_4_50_2
  doi: 10.3390/molecules16108515
– volume: 25
  start-page: 31
  year: 2012
  ident: e_1_2_4_63_2
  publication-title: Synlett
  contributor:
    fullname: Okuro K.
– ident: e_1_2_4_24_2
  doi: 10.1021/ol400472v
– ident: e_1_2_4_19_2
  doi: 10.1002/anie.200903424
– ident: e_1_2_4_42_2
  doi: 10.1039/c1ob05087g
– ident: e_1_2_4_18_2
  doi: 10.1021/cr9000836
– ident: e_1_2_4_37_2
  doi: 10.1016/j.tetlet.2004.02.086
– volume-title: Sulphones in Organic Synthesis
  year: 1993
  ident: e_1_2_4_2_2
  contributor:
    fullname: Simpkins N. S.
– ident: e_1_2_4_11_2
– ident: e_1_2_4_15_2
  doi: 10.1002/ejoc.201200572
– ident: e_1_2_4_64_2
  doi: 10.1002/adsc.201300678
– ident: e_1_2_4_57_2
  doi: 10.1002/ejoc.201001621
– volume: 12
  start-page: 167
  year: 2005
  ident: e_1_2_4_7_2
  publication-title: Curr. Med. Chem.
  contributor:
    fullname: Garuti L.
– ident: e_1_2_4_36_2
  doi: 10.1021/ja029114w
– ident: e_1_2_4_43_2
  doi: 10.1002/chem.201102811
– ident: e_1_2_4_23_2
  doi: 10.1016/j.tetlet.2009.12.035
– ident: e_1_2_4_39_2
  doi: 10.1021/jo8020715
– ident: e_1_2_4_55_2
– ident: e_1_2_4_59_2
  doi: 10.1021/co200181x
– ident: e_1_2_4_29_2
  doi: 10.1021/ol501389k
– ident: e_1_2_4_9_2
  doi: 10.1016/j.bmcl.2010.04.104
– ident: e_1_2_4_19_3
  doi: 10.1002/ange.200903424
– ident: e_1_2_4_22_2
  doi: 10.1016/j.tet.2009.01.030
– ident: e_1_2_4_17_2
  doi: 10.1021/ar0201106
– ident: e_1_2_4_41_2
  doi: 10.1021/jo101054j
– ident: e_1_2_4_6_2
– ident: e_1_2_4_16_2
– ident: e_1_2_4_35_2
  doi: 10.1002/1615-4169(200107)343:5<439::AID-ADSC439>3.0.CO;2-G
– ident: e_1_2_4_3_2
  doi: 10.1080/10426500590910657
– ident: e_1_2_4_38_2
  doi: 10.1021/jo800034m
– ident: e_1_2_4_58_2
  doi: 10.1039/c2ob25854d
– ident: e_1_2_4_12_2
  doi: 10.1021/np50076a023
– ident: e_1_2_4_40_2
  doi: 10.1039/b909701e
– ident: e_1_2_4_33_2
  doi: 10.1002/adsc.200404148
– ident: e_1_2_4_1_2
– start-page: 203
  year: 2014
  ident: e_1_2_4_60_2
  publication-title: Synthesis
  contributor:
    fullname: Xie Y.‐X.
– ident: e_1_2_4_10_2
  doi: 10.1080/10426507.2012.740703
– ident: e_1_2_4_26_2
– ident: e_1_2_4_48_2
  doi: 10.1039/b804167a
– ident: e_1_2_4_34_2
– ident: e_1_2_4_5_3
  doi: 10.1002/ange.200906340
– ident: e_1_2_4_20_2
– ident: e_1_2_4_13_2
  doi: 10.1016/j.bmc.2004.11.039
– ident: e_1_2_4_31_2
  doi: 10.1021/ol005973i
– ident: e_1_2_4_49_2
  doi: 10.2174/13895575110091235
– ident: e_1_2_4_62_2
  doi: 10.1021/cr950027e
– ident: e_1_2_4_4_2
  doi: 10.1039/b911852g
– ident: e_1_2_4_56_2
  doi: 10.1039/c0ob00835d
– ident: e_1_2_4_61_2
– ident: e_1_2_4_51_2
  doi: 10.1016/B978-0-08-096805-6.00012-7
SSID ssj0009633
Score 2.2808273
Snippet A new strategy for the synthesis of tetrahydroisoquinolines based on the Pd-0-catalyzed intramolecular -arylation of sulfones is reported. The combination of...
Abstract A new strategy for the synthesis of tetrahydroisoquinolines based on the Pd 0 ‐catalyzed intramolecular α‐arylation of sulfones is reported. The...
Source Web of Science
SourceID crossref
webofscience
SourceType Aggregation Database
Enrichment Source
Index Database
StartPage 4580
SubjectTerms Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title Pd-0-Catalyzed Intramolecular alpha-Arylation of Sulfones: Domino Reactions in the Synthesis of Functionalized Tetrahydroisoquinolines
URI http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000350760000018
Volume 21
WOS 000350760000018
WOSCitedRecordID wos000350760000018
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lj9MwELbKcoAL4inKSz7sikMViJM4D24lbLVaadFqtyvtrUr8EJW6KUrTQ3viyJG_wh_hwj_glzATJ06LilS4pJUfcZz5MjO250HIYSJcySMROgkX0gk4y5zY08zBTEgqiVUu6-OCs4_hyVVwes2ve72fG1ZLyyp_I9Y7_Ur-h6pQBnRFL9l_oKy9KRTAf6AvXIHCcN2Lxudy4A6suUKKOzGrtUL73qrMbtrEt4Oj9PjoPbPthuVqZhXFy-VM1-H6_SEo0zfTYo529cJamKNeerkq4KeJXDICQWj2D6c41FjBUJ9WspxPFyBjoD_qrYtNnTdtc8oNjGf11gFAO0fc5JnPzLF95_puGbepKNXazuI0a1x1RqosO4ifAYqXi3r_9yLTOlMmqZLd2WAcTbuM42W7RRlEDobONbKqYdAeQ6bINzm48bFukept8OOAmzxRjWzHQ-GdcsPEoYXPBIMTwJoz9F3eScjWKuAPwWnNGU3oZ2-C_Se2_y1y24sSjnamHy66mGbA8Wqzh3ZybSRR13u7Pf6WprRDK6o1oPF9cq9ZutChweED0lPFQ3LHUvcR-XouqUt_fflmkUi3kUh_fIdaiz8617TF3ztq0Ect-ui0oAA7atGHzbfRR_-CvsfkanQ8Tk-cJtOHI1iYVE4ESiXTca5CJaTwI18rj8lQaF9Gnk6CjGGiAM9XPpeMZ1GQ6wSWhoniQSBk4PtPyEEBD_uU0CQC7UMyzfwYKlSYaIHLZpfJOIdi3Sev27c6-WwCukx2069PDjdfum1tTuPxQBsXSHGfsH2apU3IfQw1UT3b-yGek7vdp_GCHFTlUr0ENbjKX9Ww-g26aLMp
link.rule.ids 315,786,790,27955,27956
linkProvider Wiley-Blackwell
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=Pd+0+%E2%80%90Catalyzed+Intramolecular+%CE%B1%E2%80%90Arylation+of+Sulfones%3A+Domino+Reactions+in+the+Synthesis+of+Functionalized+Tetrahydroisoquinolines&rft.jtitle=Chemistry+%3A+a+European+journal&rft.au=Sol%C3%A9%2C+Daniel&rft.au=P%C3%A9rez%E2%80%90Janer%2C+Ferran&rft.au=Mancuso%2C+Raffaella&rft.date=2015-03-16&rft.issn=0947-6539&rft.eissn=1521-3765&rft.volume=21&rft.issue=12&rft.spage=4580&rft.epage=4584&rft_id=info:doi/10.1002%2Fchem.201406305&rft.externalDBID=n%2Fa&rft.externalDocID=10_1002_chem_201406305
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0947-6539&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0947-6539&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0947-6539&client=summon