Synthesis of fluorinated olefins via the palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes

被引：47

作者：

Chen, C ^{[1
]}

Wilcoxen, K ^{[1
]}

Strack, N ^{[1
]}

McCarthy, JR ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 05期

关键词：

palladium catalyzed cross-coupling; fluoroolefins; oranoboranes; stereospecific;

D O I：

10.1016/S0040-4039(98)02589-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides 1-4 with organoboranes proceeds under Suzuki conditions with retention on configuration to give 1-substituted 1-fluoroolefins 6-8 in good to excellent yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：827 / 830

页数：4

共 16 条

[1] ORGANIC REACTIONS OF FLUOROXY-COMPOUNDS - STEREOCHEMISTRY OF ADDITION OF FLUOROXYTRIFLUOROMETHANE TO STILBENES
BARTON, DHR
HESSE, RH
JACKMAN, GP
OGUNKOYA, L
PECHET, MM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (07): : 739 - 742
[2] PREPARATION AND SYNTHETIC UTILITY OF FLUORINATED PHOSPHONIUM SALTS, BIS-PHOSPHONIUM SALTS AND PHOSPHORANIUM SALTS
BURTON, DJ
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1983, 23 (04) : 339 - 357
[3] Palladium/copper (I) halide-cocatalyzed stereospecific coupling of 1-fluorovinylstannanes with aryl iodides and acyl chlorides
Chen, C
Wilcoxen, K
Kim, KI
McCarthy, JR
[J]. TETRAHEDRON LETTERS, 1997, 38 (44) : 7677 - 7680
[4] SYNTHESIS OF FLUORINATED ENYNES VIA 1-BROMO-1-FLUOROALKENES
EDDARIR, S
FRANCESCH, C
MESTDAGH, H
ROLANDO, C
[J]. TETRAHEDRON LETTERS, 1990, 31 (31) : 4449 - 4452
[5] Hossain MA, 1997, TETRAHEDRON LETT, V38, P49
[6] MONOFLUORO ANALOGS OF EUGENOL METHYL-ETHER AS NOVEL ATTRACTANTS FOR THE ORIENTAL FRUIT-FLY
KHRIMIAN, AP
DEMILO, AB
WATERS, RM
LIQUIDO, NJ
NICHOLSON, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) : 8034 - 8039
[7] STEREOSELECTIVE SYNTHESIS OF (E)-ARCF=CFR AND (E)-ARCH=CFR FROM ARCH(OH)CFBR2
KUROBOSHI, M
YAMADA, N
TAKEBE, Y
HIYAMA, T
[J]. TETRAHEDRON LETTERS, 1995, 36 (35) : 6271 - 6274
[8] ANALOGS OF CELL-SURFACE CARBOHYDRATES - SYNTHESIS OF D-GALACTOSE DERIVATIVES HAVING AN ETHYNYL, VINYL OR EPOXY RESIDUE AT C-5
LEE, HH
HODGSON, PG
BERNACKI, RJ
KORYTNYK, W
SHARMA, M
[J]. CARBOHYDRATE RESEARCH, 1988, 176 (01) : 59 - 72
[9] STEREOSPECIFIC SYNTHESIS OF ALKENYL FLUORIDES (WITH RETENTION) VIA ORGANOMETALLIC INTERMEDIATES
LEE, SH
SCHWARTZ, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) : 2445 - 2447
[10] Stereospecific synthesis of 1-fluoro olefins via (fluorovinyl)stannanes and an unequivocal NMR method for the assignment of fluoro olefin geometry
McCarthy, JR
Huber, EW
Le, TB
Laskovics, FM
Matthews, DP
[J]. TETRAHEDRON, 1996, 52 (01) : 45 - 58

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