A facile synthesis of perfluoroalkyl vinyl iodides and their palladium-mediated cross-coupling reactions

被引:75
作者
Jennings, MP [1 ]
Cork, EA [1 ]
Ramachandran, PV [1 ]
机构
[1] Purdue Univ, Dept Chem, Herbert C Brown Ctr Borane Res, W Lafayette, IN 47907 USA
关键词
D O I
10.1021/jo001318c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic amounts of zinc, as low as 10 mol %, in the presence of trifluoroacetic acid (TFA) initiate the radical addition of perfluoroalkyl iodides to terminal alkynes with high regio- and stereoselectivities. Palladium-mediated cross-coupling of these (E)-perfluoroalkyl vinyl iodides allows for a. facile synthesis of potentially useful fluoroorganic intermediates.
引用
收藏
页码:8763 / 8766
页数:4
相关论文
共 30 条
[1]   ADDITION OF PERFLUOROALKYL IODIDES R(F)I (C(N)F(2N+1), N=4,6,8) TO 2-METHYL-3-BUTYN-2-OL ACTIVATED BY ZINC IN DIFFERENT SOLVENTS - APPLICATION TO THE SYNTHESIS OF PERFLUOROALKYNES [J].
ABOUGHAZALEH, B ;
LAURENT, P ;
BLANCOU, H ;
COMMEYRAS, A .
JOURNAL OF FLUORINE CHEMISTRY, 1994, 68 (01) :21-24
[2]  
BAKER DR, 1992, ACS S SERIES, V504
[3]   SYNTHESIS OF FLUORINATED ACETYLENES [J].
BAUM, K ;
BEDFORD, CD ;
HUNADI, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (12) :2251-2257
[4]   FREE RADICAL ADDITION OF IODOPERFLUOROALKANES TO BICYCLIC OLEFINS [J].
BRACE, NO .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (09) :3027-&
[5]  
Brown HC, 1999, ANGEW CHEM INT EDIT, V38, P2052, DOI 10.1002/(SICI)1521-3773(19990712)38:13/14<2052::AID-ANIE2052>3.0.CO
[6]  
2-9
[7]   Fluorinated ylides and related compounds [J].
Burton, DJ ;
Yang, ZY ;
Qiu, WM .
CHEMICAL REVIEWS, 1996, 96 (05) :1641-1715
[8]  
Filler R., 1976, ACS S SERIES, V28
[9]  
Filler R., 1982, BIOMEDICAL ASPECTS F
[10]  
FUCHIKAMI T, 1984, TETRAHEDRON LETT, V25, P303, DOI 10.1016/S0040-4039(00)99868-X