New methods for the synthesis of fluoroolefins via the palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes and organostannanes

被引：48

作者：

Chen, C ^{[1
]}

Wilcoxen, K ^{[1
]}

Huang, CQ ^{[1
]}

Strack, N ^{[1
]}

McCarthy, JR ^{[1
]}

机构：

[1] Neurocrine Biosci Inc, Dept Med Chem, San Diego, CA 92121 USA

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2000年 / 101卷 / 02期

关键词：

palladium catalyst; cross-coupling; fluoroolefin;

D O I：

10.1016/S0022-1139(99)00172-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes and organostannanes provide two new facile methods to 1-substituted 1-fluoroolefins. The reactions proceed with retention of configuration in good to excellent yields. (C) 2000 Elsevier Science S.A. All rights reserved.

引用

页码：285 / 290

页数：6

共 36 条

[1] 1,1-DIARYL- AND 1-ARYL-2-CHLORO-2-FLUOROETHYLENES [J].

ANDO, T ;

NAMIGATA, F ;

KATAOKA, M ;

YACHIDA, K ;

FUNASAKA, W .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (05) :1275-+

[2] ORGANIC REACTIONS OF FLUOROXY-COMPOUNDS - STEREOCHEMISTRY OF ADDITION OF FLUOROXYTRIFLUOROMETHANE TO STILBENES [J].

BARTON, DHR ;

HESSE, RH ;

JACKMAN, GP ;

OGUNKOYA, L ;

PECHET, MM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (07) :739-742

[3] FLUORO OLEFINS .3. SYNTHESIS OF BETA-SUBSTITUTED 1-CHLOROPERFLUORO OLEFINS [J].

BURTON, DJ ;

KRUTZSCH, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (07) :2125-&

[4] PREPARATION AND SYNTHETIC UTILITY OF FLUORINATED PHOSPHONIUM SALTS, BIS-PHOSPHONIUM SALTS AND PHOSPHORANIUM SALTS [J].

BURTON, DJ .

JOURNAL OF FLUORINE CHEMISTRY, 1983, 23 (04) :339-357

[5] Palladium/copper (I) halide-cocatalyzed stereospecific coupling of 1-fluorovinylstannanes with aryl iodides and acyl chlorides [J].

Chen, C ;

Wilcoxen, K ;

Kim, KI ;

McCarthy, JR .

TETRAHEDRON LETTERS, 1997, 38 (44) :7677-7680

[6] Synthesis of fluorinated olefins via the palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes [J].

Chen, C ;

Wilcoxen, K ;

Strack, N ;

McCarthy, JR .

TETRAHEDRON LETTERS, 1999, 40 (05) :827-830

[7] Elaboration of the side-chain of amino acid derivatives by palladium catalysed couplings [J].

Crisp, GT ;

Jiang, YL ;

Pullman, PJ ;

DeSavi, C .

TETRAHEDRON, 1997, 53 (51) :17489-17500

[8] SYNTHESIS OF FLUORINATED ENYNES VIA 1-BROMO-1-FLUOROALKENES [J].

EDDARIR, S ;

FRANCESCH, C ;

MESTDAGH, H ;

ROLANDO, C .

TETRAHEDRON LETTERS, 1990, 31 (31) :4449-4452

[9]

Eddarir S, 1997, B SOC CHIM FR, V134, P741

[10] ALPHA-FLUORO-ALPHA-ETHYLENIC KETONES - PREPARATION AND REACTION WITH DIMETHYLSULFOXONIUM METHYLIDE [J].

ELKIK, E ;

IMBEAUXOUDOTTE, M .

TETRAHEDRON LETTERS, 1985, 26 (33) :3977-3980

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