Highly substituted enynes via a palladium-catalyzed tandem three carbon-carbon bonds forming reaction procedure from benzyl halides and alkynyl tributyltin reagents

被引:9
作者
Pottier, LR [1 ]
Peyrat, JF [1 ]
Alami, M [1 ]
Brion, JD [1 ]
机构
[1] Univ Paris Sud, Fac Pharm, CNRS, Chim Therapeut Lab,UMR 8076, F-92296 Chatenay Malabry, France
关键词
Stille coupling; benzyl halides; alkynylstannanes; palladium; enynes; four-component coupling;
D O I
10.1016/j.tetlet.2004.03.173
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first report of the palladium-catalyzed cross coupling reaction of benzyl halides with alkynyl tributyltin reagents is described. This unprecedented coupling, which involves in a single reaction a tandem Stille-carbopalladation-Stille sequence allows the formation of three carbon-carbon bonds chemo-, regio- and stereoselectively and provides an efficient synthesis of highly substituted enynes. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4035 / 4038
页数:4
相关论文
共 15 条
[1]   SYNTHESIS OF ORGANOTRIALKYLSTANNANES - THE REACTION BETWEEN ORGANIC HALIDES AND HEXAALKYLDISTANNANES IN THE PRESENCE OF PALLADIUM COMPLEXES [J].
AZIZIAN, H ;
EABORN, C ;
PIDCOCK, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 215 (01) :49-58
[2]   Efficient and selective Stille cross-coupling of benzylic and allylic bromides using bromobis(triphenylphosphine) (N-succinimide)palladium(II) [J].
Crawforth, CM ;
Fairlamb, IJS ;
Taylor, RJK .
TETRAHEDRON LETTERS, 2004, 45 (03) :461-465
[3]   Bromobis(triphenylphosphine)(N-succinimide)palladium(II) as a novel catalyst for Stille cross-coupling reactions [J].
Crawforth, CM ;
Burling, S ;
Fairlamb, IJS ;
Taylor, RJK ;
Whitwood, AC .
CHEMICAL COMMUNICATIONS, 2003, (17) :2194-2195
[4]   ELABORATION OF THE SIDE-CHAIN OF ALPHA-AMINO-ACIDS BY PALLADIUM-CATALYZED STILLE COUPLINGS [J].
CRISP, GT ;
GLINK, PT .
TETRAHEDRON, 1994, 50 (10) :3213-3234
[5]   LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].
FARINA, V ;
KRISHNAN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595
[6]   ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].
FARINA, V ;
KAPADIA, S ;
KRISHNAN, B ;
WANG, CJ ;
LIEBESKIND, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5905-5911
[7]  
Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
[8]  
Fouquet E, 1998, SYNLETT, P1323
[9]   Stereoselective cross-coupling of benzylic bromides and vinyl stannanes [J].
Kamlage, S ;
Sefkow, M ;
Peter, MG .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2938-2940
[10]   PALLADIUM-CATALYZED COUPLING OF TETRAORGANOTIN COMPOUNDS WITH ARYL AND BENZYL HALIDES - SYNTHETIC UTILITY AND MECHANISM [J].
MILSTEIN, D ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4992-4998