Palladium-catalyzed α-vinylation of carbonyl compounds

被引:74
作者
Huang, Jinkun [1 ]
Bunel, Emilio [1 ]
Faul, Margaret M. [1 ]
机构
[1] Chem Proc R&D, Amgen Inc, Thousand Oaks, CA 91320 USA
关键词
D O I
10.1021/ol7019839
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild, general, catalytic system for the alpha-vinylation of carbonyl compounds has been developed. By employing [Pd((PBu3)-Bu-t)Br](2) as Catalyst and LHMDS as base, vinyl bromides, vinyl triflates, and vinyl tosylates couple with 3-methyloxindole in satisfactory yields. The same catalytic system is extended to the alpha-vinylation of ketones and esters.
引用
收藏
页码:4343 / 4346
页数:4
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共 41 条
[1]   Asymmetric arylation of ketone enolates [J].
Ahman, J ;
Wolfe, JP ;
Troutman, MV ;
Palucki, M ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1918-1919
[2]   Catalytic asymmetric vinylation of ketone enolates [J].
Chieffi, A ;
Kamikawa, K ;
Åhman, J ;
Fox, JM ;
Buchwald, SL .
ORGANIC LETTERS, 2001, 3 (12) :1897-1900
[3]   Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].
Culkin, DA ;
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245
[4]   Synthesis, characterization, and reactivity of arylpalladium cyanoalkyl complexes:: Selection of catalysts for the α-arylation of nitriles [J].
Culkin, DA ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9330-9331
[5]   Reactivity studies of [Pd2(μ-X)2(PBu3t)2] (X = Br, I) with CNR (R=2,6-dimethylphenyl), H2 and alkynes [J].
Durà-Vilà, V ;
Mingos, DMP ;
Vilar, R ;
White, AJP ;
Williams, DJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 600 (1-2) :198-205
[6]   Highly active and selective catalysts for the formation of α-aryl ketones [J].
Fox, JM ;
Huang, XH ;
Chieffi, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370
[7]   Palladium-catalyzed intramolecular α-arylation of α-amino acid esters [J].
Gaertzen, O ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :465-475
[8]   New air-stable catalysts for general and efficient Suzuki-Miyaura cross-coupling reactions of heteroaryl chlorides [J].
Guram, AS ;
King, AO ;
Allen, JG ;
Wang, XH ;
Schenkel, LB ;
Chan, J ;
Bunel, EE ;
Faul, MM ;
Larsen, RD ;
Martinelli, MJ ;
Reider, PJ .
ORGANIC LETTERS, 2006, 8 (09) :1787-1789
[9]   Palladium-catalyzed intermolecular α-arylation of zinc amide enolates under mild conditions [J].
Hama, T ;
Culkin, DA ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :4976-4985
[10]   An improved catalyst for the asymmetric arylation of ketone enolates [J].
Hamada, T ;
Chieffi, A ;
Åhman, J ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1261-1268