ACCELERATED TRANSMETALATION IN STILLE COUPLINGS EFFECTED BY CHELATION TO THE PALLADIUM

被引：20

作者：

CRISP, GT

GEBAUER, MG

机构：

[1] Department of Chemistry, The University of Adelaide, Adelaide

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 19期

关键词：

D O I：

10.1016/0040-4039(95)00489-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The relative reactivities of vinylstannanes 2a,b and 4a,b in a Stille coupling with vinyl bromide were studied under a variety of conditions. Vinyl bromide coupled with the sterically hindered vinylstannane 2a preferentially compared to the less hindered stannane 2b when PdCl2(CH3CN)(2) was employed as a catalyst. Coordination of the nitrogen of the imine protecting group to the palladium is proposed to account for this rate acceleration.

引用

收藏

页码：3389 / 3392

页数：4

相关论文

共 14 条

[1] INTIMATE MECHANISM OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES IN THE PRESENCE OF HALIDE-IONS AND ITS RELEVANCE TO THE MECHANISM OF PALLADIUM-CATALYZED NUCLEOPHILIC SUBSTITUTIONS [J].

AMATORE, C ;

JUTAND, A ;

SUAREZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9531-9541

[2] THE CROSS-COUPLING REACTIONS OF ORGANIC HALIDES WITH ORGANIC DERIVATIVES OF TIN, MERCURY AND COPPER CATALYZED BY PALLADIUM [J].

BELETSKAYA, IP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 250 (01) :551-564

[3]

COLLMAN JP, 1987, PRINCIPLES APPLICATI

[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]

MITCHELL TN, 1992, SYNTHESIS-STUTTGART, P803

[7] PALLADIUM CATALYZED CROSS-COUPLING REACTIONS OF ALKENYL (PHENYL) IODONIUM SALTS WITH ORGANOTIN COMPOUNDS [J].

MORIARTY, RM ;

EPA, WR .

TETRAHEDRON LETTERS, 1992, 33 (29) :4095-4098

[8] NICKEL-CATALYZED OR PALLADIUM-CATALYZED CROSS COUPLING .31. PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTIONS OF ALKENYLMETALS WITH UNSATURATED ORGANIC HALIDES AS A SELECTIVE ROUTE TO ARYLATED ALKENES AND CONJUGATED DIENES - SCOPE, LIMITATIONS, AND MECHANISM [J].

NEGISHI, E ;

TAKAHASHI, T ;

BABA, S ;

VANHORN, DE ;

OKUKADO, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2393-2401

[9] TOTAL SYNTHESIS OF RAPAMYCIN [J].

NICOLAOU, KC ;

CHAKRABORTY, TK ;

PISCOPIO, AD ;

MINOWA, N ;

BERTINATO, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4419-4420

[10]

SEEBACH D, 1982, HELV CHIM ACTA, V65, P385