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

被引:43
作者
Chen, C [1 ]
Wilcoxen, K [1 ]
Kim, KI [1 ]
McCarthy, JR [1 ]
机构
[1] NEUROCRINE BIOSCI INC,DEPT MED CHEM,SAN DIEGO,CA 92129
关键词
D O I
10.1016/S0040-4039(97)10003-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cross-coupling of 1-fluorovinylstannanes with aryl iodides or acyl chlorides, cocatalyzed by palladium and copper (I) iodide proceeded under mild conditions to give substituted fluoro olefins and alpha-fluoro-alpha,beta-unsaturated ketones, respectively, in good yields with retention of configuration. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7677 / 7680
页数:4
相关论文
共 17 条
[1]  
[Anonymous], 1991, Fluorine in Bioorganic Chemistry
[2]  
Banks R.E., 1994, ORGANOFLUORINE CHEM
[3]   PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].
ECHAVARREN, AM ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1557-1565
[4]  
Emsley J.M., 1977, FLUORINE COUPLING CO
[5]   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
[6]  
FILLER R, 1993, ORGANOFLUROINE COMPO
[7]   A NOVEL AND EFFICIENT SYNTHESIS OF FLUOROMETHYL PHENYL SULFONE AND ITS USE AS A FLUOROMETHYL WITTIG EQUIVALENT [J].
INBASEKARAN, M ;
PEET, NP ;
MCCARTHY, JR ;
LETOURNEAU, ME .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) :678-679
[8]  
MAN J, 1987, CHEM SOC REV, V16, P381
[9]   THE SYNTHESIS OF (1-FLUOROVINYL)TRIBUTYLTIN - A SYNTHETIC EQUIVALENT FOR THE 1-FLUOROETHENE ANION [J].
MATTHEWS, DP ;
WAID, PP ;
SABOL, JS ;
MCCARTHY, JR .
TETRAHEDRON LETTERS, 1994, 35 (29) :5177-5180
[10]   A NEW ROUTE TO 2-FLUORO-1-OLEFINS UTILIZING A SYNTHETIC EQUIVALENT FOR THE 1-FLUOROETHENE ANION [J].
MATTHEWS, DP ;
GROSS, RS ;
MCCARTHY, JR .
TETRAHEDRON LETTERS, 1994, 35 (07) :1027-1030