Aerobic Oxidative Heck/Dehydrogenation Reactions of Cyclohexenones: Efficient Access to meta-Substituted Phenols

Ein vielseitiger dikationischer Palladium(II)‐Katalysator mit 6,6′‐Dimethyl‐2,2′‐bipyridin als Ligand vermittelt sowohl aerobe oxidative Heck‐Kupplungen als auch Dehydrierungen von Cyclohexenonen. Diese Reaktionen können für die direkte Synthese meta‐substituierter Phenole zu einer Eintopfsequenz ko...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie Vol. 125; no. 13; pp. 3760 - 3763
Main Authors Izawa, Yusuke, Zheng, Changwu, Stahl, Shannon S.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 25.03.2013
WILEY‐VCH Verlag
Subjects
Online AccessGet full text

Cover

Loading…
Abstract Ein vielseitiger dikationischer Palladium(II)‐Katalysator mit 6,6′‐Dimethyl‐2,2′‐bipyridin als Ligand vermittelt sowohl aerobe oxidative Heck‐Kupplungen als auch Dehydrierungen von Cyclohexenonen. Diese Reaktionen können für die direkte Synthese meta‐substituierter Phenole zu einer Eintopfsequenz kombiniert werden (siehe Schema).
AbstractList Ein vielseitiger dikationischer Palladium(II)‐Katalysator mit 6,6′‐Dimethyl‐2,2′‐bipyridin als Ligand vermittelt sowohl aerobe oxidative Heck‐Kupplungen als auch Dehydrierungen von Cyclohexenonen. Diese Reaktionen können für die direkte Synthese meta‐substituierter Phenole zu einer Eintopfsequenz kombiniert werden (siehe Schema).
Author Zheng, Changwu
Izawa, Yusuke
Stahl, Shannon S.
Author_xml – sequence: 1
  givenname: Yusuke
  surname: Izawa
  fullname: Izawa, Yusuke
  organization: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA)
– sequence: 2
  givenname: Changwu
  surname: Zheng
  fullname: Zheng, Changwu
  organization: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA)
– sequence: 3
  givenname: Shannon S.
  surname: Stahl
  fullname: Stahl, Shannon S.
  email: stahl@chem.wisc.edu
  organization: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA)
BookMark eNo9kMtuwjAQRa2KSgXabdf-gYDtPBx3FwENrRD0qS4tx5mACyQoNi35-yaiYjUzV3NGozNAvbIqAaF7SkaUEDZW5RpGjFBGRBDyK9SnIaOez0PeQ31CgsCLWSBu0MDab0JIxLjoo0MCdZUZjVcnkytnfgDPQW_HU9g0eV2toWzDqsRvoHTXWFwVeNLoXbWBE3Qf2Ac8KwqjDZQOJ1qDtdhVeA9Oee_HzDrjjg5y_LJp13f2Fl0Xamfh7r8O0efj7GMy9xar9GmSLDxNheBeAVGgFHAe5aAzoUWsijxWESORZiHjRZRnecaywo8I59qPOQdC_Yxy6ucZhP4QifPdX7ODRh5qs1d1IymRnSzZyZIXWTJZprPL1LLemTXWwenCqnorI94KlV_LVPoiToPn8FVO_T_1KXPg
CitedBy_id crossref_primary_10_1002_adsc_201801058
crossref_primary_10_1002_anie_201307471
crossref_primary_10_1002_ange_201311103
crossref_primary_10_1002_adsc_201300707
crossref_primary_10_1002_adsc_202001053
crossref_primary_10_1039_c3ra43071e
crossref_primary_10_1002_anie_201308260
crossref_primary_10_1002_ange_201305019
crossref_primary_10_1021_acs_orglett_8b01484
crossref_primary_10_1002_ange_202105355
crossref_primary_10_1039_C4CC07997C
crossref_primary_10_1002_anie_201507134
crossref_primary_10_1002_adsc_201701068
crossref_primary_10_1039_C4CC08370A
crossref_primary_10_1002_cctc_201402075
crossref_primary_10_1002_ange_201506751
crossref_primary_10_1002_ange_201308260
crossref_primary_10_1002_anie_201311103
crossref_primary_10_1002_cctc_201700370
crossref_primary_10_1002_adsc_201500573
crossref_primary_10_1002_cctc_201600447
crossref_primary_10_1039_C7OB01114H
crossref_primary_10_1002_ajoc_201700208
crossref_primary_10_1002_adsc_201800778
crossref_primary_10_1002_chem_201402063
crossref_primary_10_1002_chem_201704442
crossref_primary_10_1002_adsc_201800258
crossref_primary_10_1002_ange_201307471
crossref_primary_10_1002_chem_201702651
crossref_primary_10_1002_cctc_201500079
crossref_primary_10_1039_C4OB00714J
crossref_primary_10_1002_chem_201703642
crossref_primary_10_1002_anie_202105355
crossref_primary_10_1002_cctc_201402781
crossref_primary_10_1002_ange_201507134
crossref_primary_10_1002_anie_201305019
crossref_primary_10_1002_anie_201506751
ContentType Journal Article
Copyright Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Copyright_xml – notice: Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
DBID BSCLL
DOI 10.1002/ange.201209457
DatabaseName Istex
DatabaseTitleList
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1521-3757
EndPage 3763
ExternalDocumentID ANGE201209457
ark_67375_WNG_398G4J5Q_D
Genre shortCommunication
GrantInformation_xml – fundername: Shanghai Institute of Organic Chemistry
– fundername: Mitsubishi Chemical Corporation
– fundername: NIH
  funderid: R01 GM100143
GroupedDBID -~X
.3N
.GA
.Y3
05W
0R~
10A
1L6
1OB
1OC
1ZS
33P
3SF
3WU
4.4
50Y
50Z
51W
51X
52M
52N
52O
52P
52S
52T
52U
52W
52X
5VS
66C
6P2
702
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
ABEML
ABHUG
ABIJN
ABJNI
ABLJU
ABPVW
ACAHQ
ACBWZ
ACCFJ
ACCUC
ACCZN
ACGFS
ACIWK
ACNCT
ACPOU
ACPRK
ACSCC
ACXBN
ACXME
ACXQS
ADAWD
ADBBV
ADDAD
ADEOM
ADIZJ
ADKYN
ADMGS
ADOZA
ADXAS
ADZMN
ADZOD
AEEZP
AEIGN
AEIMD
AEQDE
AEUQT
AEUYR
AFBPY
AFFPM
AFGKR
AFPWT
AFRAH
AFVGU
AGJLS
AHBTC
AIURR
AIWBW
AJBDE
AJXKR
ALAGY
ALMA_UNASSIGNED_HOLDINGS
ALUQN
AMBMR
AMYDB
ASPBG
ATUGU
AUFTA
AVWKF
AZBYB
AZFZN
AZVAB
BAFTC
BDRZF
BFHJK
BHBCM
BMNLL
BMXJE
BNHUX
BROTX
BRXPI
BSCLL
BY8
CS3
D-E
D-F
DCZOG
DPXWK
DR2
DRFUL
DRSTM
EBS
EJD
F00
F01
F04
F5P
G-S
G.N
GNP
GODZA
H.T
H.X
HHY
HHZ
HZ~
IX1
J0M
JPC
KQQ
LATKE
LAW
LC2
LC3
LEEKS
LITHE
LOXES
LP6
LP7
LUTES
LYRES
MEWTI
MK4
MRFUL
MRSTM
MSFUL
MSSTM
MXFUL
MXSTM
N04
N05
N9A
NF~
O66
O9-
P2W
P2X
P4D
Q.N
Q11
QB0
QRW
R.K
RGC
ROL
RWI
RX1
RYL
SUPJJ
TN5
TUS
UB1
UPT
V2E
W8V
W99
WBFHL
WBKPD
WIH
WIK
WJL
WOHZO
WQJ
WRC
WXSBR
WYISQ
XG1
XV2
Y6R
ZZTAW
~IA
~WT
AITYG
HGLYW
OIG
ID FETCH-LOGICAL-c1997-fe64aae776decb9c98afd8a6206c2527f6dbdb2bf36077c3877e013b1713dbe53
IEDL.DBID DR2
ISSN 0044-8249
IngestDate Sat Aug 24 00:59:26 EDT 2024
Wed Jan 17 05:00:41 EST 2024
IsPeerReviewed true
IsScholarly true
Issue 13
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c1997-fe64aae776decb9c98afd8a6206c2527f6dbdb2bf36077c3877e013b1713dbe53
Notes Shanghai Institute of Organic Chemistry
ark:/67375/WNG-398G4J5Q-D
NIH - No. R01 GM100143
Mitsubishi Chemical Corporation
istex:1E0D02E95F18D5F1AE104ADAFD45648165DCAB65
ArticleID:ANGE201209457
We thank Dr. Doris Pun for assistance in product purification. Financial support was provided by the NIH (R01 GM100143), Mitsubishi Chemical Corporation, and the Shanghai Institute of Organic Chemistry (postdoctoral fellowship for C.W.Z.).
These authors contributed equally to this work.
PageCount 4
ParticipantIDs wiley_primary_10_1002_ange_201209457_ANGE201209457
istex_primary_ark_67375_WNG_398G4J5Q_D
PublicationCentury 2000
PublicationDate March 25, 2013
PublicationDateYYYYMMDD 2013-03-25
PublicationDate_xml – month: 03
  year: 2013
  text: March 25, 2013
  day: 25
PublicationDecade 2010
PublicationPlace Weinheim
PublicationPlace_xml – name: Weinheim
PublicationTitle Angewandte Chemie
PublicationTitleAlternate Angew. Chem
PublicationYear 2013
Publisher WILEY-VCH Verlag
WILEY‐VCH Verlag
Publisher_xml – name: WILEY-VCH Verlag
– name: WILEY‐VCH Verlag
References Y. Fall, H. Doucet, M. Santelli, Tetrahedron 2009, 65, 489
T. Imahori, T. Tokuda, T. Taguchi, H. Takahata, Org. Lett. 2012, 14, 1172
Y. Moon, D. Kwon, S. Hong, Angew. Chem. 2012, 124, 11495
P. A. Enquist, J. Lindh, P. Nilsson, M. Larhed, Green Chem. 2006, 8, 338
For a review, see: B. Karimi, H. Behzadnia, D. Elhamifar, P. F. Akhavan, F. K. Esfahani, A. Zamani, Synthesis 2010, 1399.
D. Fegley, S. Gaetani, A. Duranti, A. Tontini, M. Mor, G. Tarzia, D. Piomelli, J. Pharmacol. Exp. Ther. 2005, 313, 352
J. H. Delcamp, A. P. Brucks, M. C. White, J. Am. Chem. Soc. 2008, 130, 11270
For previous use of AMS as a cocatalyst in a palladium-catalyzed oxidation reaction, see: R. A. Sheldon, J. M. Sobczak, J. Mol. Catal. 1991, 68, 1.
H. A. Duong, R. E. Gilligan, M. L. Cooke, R. J. Phipps, M. J. Gaunt, Angew. Chem. 2011, 123, 483
R. A. Davis, A. Hofmann, A. Osman, R. A. Hall, F. A. Mühlschlegel, D. Vullo, A. Innocenti, C. T. Supuran, S. Poulsen, J. Med. Chem. 2011, 54, 1682.
J. Muzart, Eur. J. Org. Chem. 2010, 3779.
A. Tlili, N. Xia, F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 8881
For previous syntheses, see: M. Mor, S. Rivara, A. Lodola, P. V. Plazzi, G. Tarzia, A. Duranti, A. Tontini, G. Piersanti, S. Kathuria, D. Piomelli, J. Med. Chem. 2004, 47, 4998.
X.-F. Xia, X.-Z. Shu, K.-G. Ji, Y.-F. Yang, A. Shaukat, X.-Y. Liu, Y.-M. Liang, J. Org. Chem. 2010, 75, 2893
K. W. Anderson, T. Ikawa, R. E. Tundel, S. L. Buchwald, J. Am. Chem. Soc. 2006, 128, 10694
Angew. Chem. Int. Ed. 2012, 51, 7537
J.-Y. Cho, C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 2000, 122, 12868
A. L. Gottumukkala, J. F. Teichert, D. Heijnen, N. Eisink, S. Van Dijk, C. Ferrer, A. J. Minnaard, A. Van Den Hoogenband, J. Org. Chem. 2011, 76, 3498.
M. V. Leskinen, K. T. Yip, A. Valkonen, P. M. Pihko, J. Am. Chem. Soc. 2012, 134, 5750.
E. W. Werner, M. S. Sigman, J. Am. Chem. Soc. 2010, 132, 13981
R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593
Angew. Chem. Int. Ed. 2012, 51, 784
A. Hajra, Y. Wei, N. Yoshikai, Org. Lett. 2012, 14, 5488
T. R. Krishna, N. Jayaraman, Tetrahedron 2004, 60, 10325
E. C. Horning, M. G. Horning, J. Am. Chem. Soc. 1947, 69, 1359
T. Diao, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 14566
J. Lindh, P. Enquist, Å. Pilotti, P. Nilsson, M. Larhed, J. Org. Chem. 2007, 72, 7957
J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, M. R. Smith III, Science 2002, 295, 305
H. E. Zimmerman, E. E. Nesterov, J. Am. Chem. Soc. 2003, 125, 5422
T. Ishiyama, J. Takagi, J. F. Hartwig, N. Miyaura, Angew. Chem. 2002, 114, 3182
P. M. Dewick, Medicinal Natural Products: A Biosynthetic Approach, Wiley-VCH, Weinheim, 2011
K. S. Yoo, C. P. Park, C. H. Yoon, S. Sakaguchi, J. O'Neill, K. W. Jung, Org. Lett. 2007, 9, 3933
Y. H. Zhang, J. Q. Yu, J. Am. Chem. Soc. 2009, 131, 14654
K. T. Yip, R. Y. Nimje, M. V. Leskinen, P. M. Pihko, Chem. Eur. J. 2012, 18, 12590
R. E. Maleczka, Jr., F. Shi, D. Holmes, M. R. Smith III, J. Am. Chem. Soc. 2003, 125, 7792
Y. Q. Zou, J. R. Chen, X. P. Liu, L. Q. Lu, R. L. Davis, K. A. Jørgensen, W. J. Xiao, Angew. Chem. 2012, 124, 808
T. Diao, T. J. Wadzinski, S. S. Stahl, Chem. Sci. 2012, 3, 887.
T. Hirao, M. Mori, Y. Ohshiro, J. Org. Chem. 1990, 55, 358
C. H. Yoon, K. S. Yoo, S. W. Yi, R. K. Mishra, K. W. Jung, Org. Lett. 2004, 6, 4037
J. Matsuo, Y. Aizawa, Chem. Commun. 2005, 2399
I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
D. Leow, G. Li, T. S. Mei, J. Q. Yu, Nature 2012, 486, 518.
D. Piomelli, G. Tarzia, A. Duranti, A. Tontini, M. Mor, T. R. Compton, O. Dasse, E. P. Monaghan, J. A. Parrott, D. Putman, CNS Drug Rev. 2006, 12, 21.
Angew. Chem. Int. Ed. 2012, 51, 11333
C. W. Yu, G. S. Chen, C. W. Huang, J. W. Chern, Org. Lett. 2012, 14, 3688.
M. M. S. Andappan, P. Nilsson, M. Larhed, Chem. Commun. 2004, 218
K. W. Quasdorf, M. Riener, K. V. Petrova, N. K. Garg, J. Am. Chem. Soc. 2009, 131, 17748.
S. Kathuria, S. Gaetani, D. Fegley, F. Valiño, A. Duranti, A. Tontini, M. Mor, G. Tarzia, G. La Rana, A. Calignano, A. Giustino, M. Tattoli, M. Palmery, V. Cuomo, D. Piomelli, Nat. Med. 2002, 9, 76
S. R. Kandukuri, M. Oestreich, J. Org. Chem. 2012, 77, 8750
A. N. Campbell, P. B. White, I. A. Guzei, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 15116
A. N. Campbell, E. B. Meyer, S. S. Stahl, Chem. Commun. 2011, 47, 10257.
Y. Xie, S. Liu, Y. Liu, Y. Wen, G. J. Deng, Org. Lett. 2012, 14, 1692.
Angew. Chem. Int. Ed. 2009, 48, 8725
C. W. Zheng, D. Wang, S. S. Stahl, J. Am. Chem. Soc. 2012, 134, 16496.
S. A. Girard, X. Hu, T. Knauber, F. Zhou, M. Simon, G. J. Deng, C. J. Li, Org. Lett. 2012, 14, 5606
O. Saidi, J. Marafie, A. E. W. Ledger, P. M. Liu, M. F. Mahon, G. Kociok-Köhn, M. K. Whittlesey, C. G. Frost, J. Am. Chem. Soc. 2011, 133, 19298
T. Moriuchi, K. Kikushima, T. Kajikawa, T. Hirao, Tetrahedron Lett. 2009, 50, 7385; For a review, see
Y. Izawa, D. Pun, S. S. Stahl, Science 2011, 333, 209
M. M. S. Andappan, P. Nilsson, H. von Schenck, M. Larhed, J. Org. Chem. 2004, 69, 5212
J. H. P. Tyman, Synthetic and Natural Phenols, Elsevier, New York, 1996
Angew. Chem. Int. Ed. 2011, 50, 463
S. Maurer, Y. W. Jiang, D. W. Ma, W. Liu, X. J. Zhang, Synlett 2010, 976
C. Hoarau, T. R. R. Pettus, Synlett 2003, 127
Y. Shvo, A. H. I. Arisha, J. Org. Chem. 1998, 63, 5640
J. Ruan, X. Li, O. Saidi, J. Xiao, J. Am. Chem. Soc. 2008, 130, 2424
Y. H. Zhang, B. F. Shi, J. Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072.
K. S. Yoo, C. H. Yoon, K. W. Jung, J. Am. Chem. Soc. 2006, 128, 16384
T. Ohmura, A. Kijima, M. Suginome, J. Am. Chem. Soc. 2009, 131, 6070
T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 390
M. Simon, S. A. Girard, C. J. Li, Angew. Chem. 2012, 124, 7655
Angew. Chem. Int. Ed. 2002, 41, 3056
2011; 333
2010; 75
1990; 55
2002 2002; 114 41
2012; 486
2009; 65
2004; 60
1947; 69
2002; 9
2006; 12
2011
2010
2002; 295
2004; 69
2004; 47
2005; 313
2006; 8
1996
2004; 6
2011; 54
2011; 76
2012; 18
2005
2004
2007; 72
2003
2011 2011; 123 50
2009; 131
2012; 14
1998; 63
2012; 77
2011; 133
2009 2009; 121 48
2012; 3
2012; 134
1991; 68
2009; 50
2002; 124
2010; 132
2007; 9
2012 2012; 124 51
2000; 122
2000; 100
2011; 47
2003; 125
2006; 128
2009; 323
2008; 130
References_xml – year: 2011
– volume: 18
  start-page: 12590
  year: 2012
  publication-title: Chem. Eur. J.
– volume: 69
  start-page: 5212
  year: 2004
  publication-title: J. Org. Chem.
– volume: 333
  start-page: 209
  year: 2011
  publication-title: Science
– volume: 486
  start-page: 518
  year: 2012
  publication-title: Nature
– volume: 134
  start-page: 5750
  year: 2012
  publication-title: J. Am. Chem. Soc.
– volume: 47
  start-page: 10257
  year: 2011
  publication-title: Chem. Commun.
– start-page: 3779
  year: 2010
  publication-title: Eur. J. Org. Chem.
– start-page: 218
  year: 2004
  publication-title: Chem. Commun.
– volume: 132
  start-page: 13981
  year: 2010
  publication-title: J. Am. Chem. Soc.
– volume: 14
  start-page: 3688
  year: 2012
  publication-title: Org. Lett.
– volume: 54
  start-page: 1682
  year: 2011
  publication-title: J. Med. Chem.
– volume: 100
  start-page: 3009
  year: 2000
  publication-title: Chem. Rev.
– volume: 9
  start-page: 76
  year: 2002
  publication-title: Nat. Med.
– volume: 295
  start-page: 305
  year: 2002
  publication-title: Science
– volume: 14
  start-page: 1172
  year: 2012
  publication-title: Org. Lett.
– start-page: 1399
  year: 2010
  publication-title: Synthesis
– volume: 323
  start-page: 1593
  year: 2009
  publication-title: Science
– volume: 133
  start-page: 19298
  year: 2011
  publication-title: J. Am. Chem. Soc.
– volume: 14
  start-page: 1692
  year: 2012
  publication-title: Org. Lett.
– volume: 12
  start-page: 21
  year: 2006
  publication-title: CNS Drug Rev.
– volume: 6
  start-page: 4037
  year: 2004
  publication-title: Org. Lett.
– volume: 72
  start-page: 7957
  year: 2007
  publication-title: J. Org. Chem.
– volume: 124 51
  start-page: 11495 11333
  year: 2012 2012
  publication-title: Angew. Chem. Angew. Chem. Int. Ed.
– volume: 131
  start-page: 17748
  year: 2009
  publication-title: J. Am. Chem. Soc.
– volume: 68
  start-page: 1
  year: 1991
  publication-title: J. Mol. Catal.
– volume: 313
  start-page: 352
  year: 2005
  publication-title: J. Pharmacol. Exp. Ther.
– volume: 14
  start-page: 5488
  year: 2012
  publication-title: Org. Lett.
– volume: 14
  start-page: 5606
  year: 2012
  publication-title: Org. Lett.
– volume: 125
  start-page: 5422
  year: 2003
  publication-title: J. Am. Chem. Soc.
– volume: 65
  start-page: 489
  year: 2009
  publication-title: Tetrahedron
– start-page: 127
  year: 2003
  publication-title: Synlett
– volume: 128
  start-page: 16384
  year: 2006
  publication-title: J. Am. Chem. Soc.
– volume: 130
  start-page: 2424
  year: 2008
  publication-title: J. Am. Chem. Soc.
– volume: 69
  start-page: 1359
  year: 1947
  publication-title: J. Am. Chem. Soc.
– volume: 131
  start-page: 6070
  year: 2009
  publication-title: J. Am. Chem. Soc.
– volume: 124 51
  start-page: 7655 7537
  year: 2012 2012
  publication-title: Angew. Chem. Angew. Chem. Int. Ed.
– volume: 124 51
  start-page: 808 784
  year: 2012 2012
  publication-title: Angew. Chem. Angew. Chem. Int. Ed.
– volume: 130
  start-page: 11270
  year: 2008
  publication-title: J. Am. Chem. Soc.
– year: 1996
– volume: 134
  start-page: 16496
  year: 2012
  publication-title: J. Am. Chem. Soc.
– volume: 9
  start-page: 3933
  year: 2007
  publication-title: Org. Lett.
– volume: 131
  start-page: 14654
  year: 2009
  publication-title: J. Am. Chem. Soc.
– volume: 125
  start-page: 7792
  year: 2003
  publication-title: J. Am. Chem. Soc.
– volume: 8
  start-page: 338
  year: 2006
  publication-title: Green Chem.
– volume: 124
  start-page: 390
  year: 2002
  publication-title: J. Am. Chem. Soc.
– volume: 128
  start-page: 10694
  year: 2006
  publication-title: J. Am. Chem. Soc.
– volume: 131
  start-page: 5072
  year: 2009
  publication-title: J. Am. Chem. Soc.
– volume: 63
  start-page: 5640
  year: 1998
  publication-title: J. Org. Chem.
– volume: 47
  start-page: 4998
  year: 2004
  publication-title: J. Med. Chem.
– volume: 50
  start-page: 7385
  year: 2009
  publication-title: Tetrahedron Lett.
– volume: 77
  start-page: 8750
  year: 2012
  publication-title: J. Org. Chem.
– volume: 75
  start-page: 2893
  year: 2010
  publication-title: J. Org. Chem.
– volume: 55
  start-page: 358
  year: 1990
  publication-title: J. Org. Chem.
– volume: 133
  start-page: 14566
  year: 2011
  publication-title: J. Am. Chem. Soc.
– volume: 3
  start-page: 887
  year: 2012
  publication-title: Chem. Sci.
– volume: 132
  start-page: 15116
  year: 2010
  publication-title: J. Am. Chem. Soc.
– volume: 122
  start-page: 12868
  year: 2000
  publication-title: J. Am. Chem. Soc.
– start-page: 2399
  year: 2005
  publication-title: Chem. Commun.
– volume: 121 48
  start-page: 8881 8725
  year: 2009 2009
  publication-title: Angew. Chem. Angew. Chem. Int. Ed.
– volume: 76
  start-page: 3498
  year: 2011
  publication-title: J. Org. Chem.
– volume: 114 41
  start-page: 3182 3056
  year: 2002 2002
  publication-title: Angew. Chem. Angew. Chem. Int. Ed.
– volume: 123 50
  start-page: 483 463
  year: 2011 2011
  publication-title: Angew. Chem. Angew. Chem. Int. Ed.
– start-page: 976
  year: 2010
  publication-title: Synlett
– volume: 60
  start-page: 10325
  year: 2004
  publication-title: Tetrahedron
SSID ssj0006279
Score 1.8734779
Snippet Ein vielseitiger dikationischer Palladium(II)‐Katalysator mit 6,6′‐Dimethyl‐2,2′‐bipyridin als Ligand vermittelt sowohl aerobe oxidative Heck‐Kupplungen als...
SourceID wiley
istex
SourceType Publisher
StartPage 3760
SubjectTerms Dehydrierungen
Heck-Reaktion
Oxidationen
Palladium
Synthesemethoden
Title Aerobic Oxidative Heck/Dehydrogenation Reactions of Cyclohexenones: Efficient Access to meta-Substituted Phenols
URI https://api.istex.fr/ark:/67375/WNG-398G4J5Q-D/fulltext.pdf
https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fange.201209457
Volume 125
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpZ1LT9wwEMcttD3QSx-0VSkF-YB6C5u1HTvmFvapldgWBOreIj8m2mopQdkgLZz6EfiMfBJsh11Kj_QYKZas8djzn2T8G4T2eSG1Cyw6EiqmERNxEclEsohQZo2kICD8PT-e8NE5G0-T6V-3-Bs-xPqDm98Z4bz2G1zpRfsJGupr731pFnEJSuKvk3uanldFp0_8KE4a2F7MWJS6RGNFbYxJ-_lwJ029VZfPJWqIMYO3SK1m15SWzA-ua31gbv8BN_7P9N-hN48CFGeNx7xHG3C5hTa7q75vH1CVgWczGfx9-csGLDgegZm3ezC7sVXpHC4sJj6F5k7EApcF7t6Yi3IGS7j07P9D3A9kChfQcBY6MuK6xL-hVvd_7vxR1dQnWPxj5gZcLD6i80H_rDuKHjszRCbgWwvgTCkQglswWhqZqsKmipOYG5IQUXCrrSa6oDwWwtBUCHBaU3dcSmw1JPQTavn5fEZYxQCUCKFc0GCKpNpK0oFCWMGdcgW5jb6FlcmvGvpGrqq5L0YTSf5zMsypTIdsnJzkvW1Egr3XLzZAZpJ7S-drS-fZZNhfP315yaAd9JqEphg0IslX1Kqra9h10qTWe-hVdtQ7GuwFN3wAftff3w
link.rule.ids 315,786,790,1382,27957,27958,46329,46753
linkProvider Wiley-Blackwell
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpZ1LTxsxEIAtCAe4QGmLGmiLD1VvSxY_171FISTlkbYIVG6WH7NKFSAoWaTQU39Cf2N_SW0vCaLHclxpLXnHM54Z7_gbhD6IUtngWGwmTU4zJvMyU1yxjFDmnaIgIf09Px2I_gU7uuTzasJ4F6bmQywO3KJlpP06Gng8kG49UkNj8X2szSIhQ-FyGa0Em-cpqzp7JEgJUuP2csayIqQac25jTlpPx4fgNMp19jRITV7mcAPZ-fzq4pLR3l1l99zPf9CNz_qAF2j9IQbF7VppNtES3LxEq51567dXaNKGiGdy-Mvsh09kcNwHN2odwPDeT8ZB59J64jOor0VM8bjEnXt3NR7CDG4i_v8T7iY4RfBpuJ2aMuJqjK-hMn9-_Y67VV2i4PHXYRhwNX2NLg67551-9tCcIXOJ4FqCYMaAlMKDs8qpwpS-MILkwhFOZCm89ZbYkopcSkcLKSGEm3Y_ZMXeAqdbqBHn8wZhkwNQIqUJfoMZUlivyD6U0ksRgldQTfQxLY2-rQEc2kxGsR5Ncv190NNUFT12xL_pgyYiSeCLF2smM9FR0nohad0e9LqLp-3_GbSLVvvnpyf65PPgeAetkdQjg2aEv0WNanIH70KkUtn3SRf_AoPL4o8
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpZ1fTxQxEMAbxUR9UVEJJ6J9IL4tt7Tddsvb5f4KeiCRyFvTP9McOeQux5IcPvkR-Ix8Etoud4iP-rjJTjKZTjszu9PfILTFvTQhsJhM6JxmTOQ-k4VkGaHMWUlBQPp7_nXIB8ds76Q4-eMWf82HWH5wizsjnddxg0-db95DQ2PvfWzNIqFAKcRj9IRxSqJfd47uAVKc1LS9nLGsDJXGAtuYk-ZD-ZCbRrPOH-aoKcj0XiK9UK_uLRlvX1Zm2_76i9z4P_q_Qi_uMlDcql1mFT2C89foWXsx-O0NmrUgwpksPpifusQFxwOw42YHRlduNgkel1YTH0F9KeICTzxuX9mzyQjmcB7h_7u4m9AUIaLhVhrJiKsJ_gmVvvl9Hc-qukHB4cNREDi7eIuOe93v7UF2N5ohs4nf6oEzrUEI7sAaaWWpvSs1Jzm3pCDCc2ecIcZTngthaSkEhGTT7ISa2Bko6BpaifqsI6xzAEqE0CFqME1K4yTZAS-c4CF1BdlAn9LKqGmN31B6No7daKJQP4Z9RWXZZ3vFN9VpIJLsvXyxJjITFS2tlpZWrWG_u3x69y9CH9HTw05Pffk83N9Az0kakEEzUrxHK9XsEjZDmlKZD8kTbwH5LeE-
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=Aerobic+Oxidative+Heck%2FDehydrogenation+Reactions+of+Cyclohexenones%3A+Efficient+Access+to+meta-Substituted+Phenols&rft.jtitle=Angewandte+Chemie&rft.au=Izawa%2C+Yusuke&rft.au=Zheng%2C+Changwu&rft.au=Stahl%2C+Shannon+S.&rft.date=2013-03-25&rft.pub=WILEY-VCH+Verlag&rft.issn=0044-8249&rft.eissn=1521-3757&rft.volume=125&rft.issue=13&rft.spage=3760&rft.epage=3763&rft_id=info:doi/10.1002%2Fange.201209457&rft.externalDBID=n%2Fa&rft.externalDocID=ark_67375_WNG_398G4J5Q_D
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0044-8249&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0044-8249&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0044-8249&client=summon