Suzuki arylation of 1,1-dibromo-1-alkenes: Synthesis of tetra-substituted alkenes

被引:37
作者
Bauer, A [1 ]
Miller, MW [1 ]
Vice, SF [1 ]
McCombie, SW [1 ]
机构
[1] Schering Plough Corp, Res Inst, Dept Chem Res, Kenilworth, NJ 07033 USA
关键词
Suzuki reaction; cross-coupling; arylations; palladium; alkenes;
D O I
10.1055/s-2001-10776
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,1-Dibromo-1-alkenes were coupled with a variety of aryl boronic acids using Suzuki conditions (PdCl2(PPh3)(2)/Na2CO3/ THF-H2O or DME-H2O/65-90 degreesC). The 1,1-dibromo-1-alkenes were prepared from ketones, and thus, the overall process furnished tetra-substituted alkenes in a very efficient manner.
引用
收藏
页码:254 / 256
页数:3
相关论文
共 21 条
[1]  
BALDWIN JE, 1995, TETRAHEDRON LETT, V36, P9951
[2]  
Eymery F, 2000, SYNTHESIS-STUTTGART, P185
[3]  
Hanisch I, 2000, SYNLETT, P374
[4]   The interaction of pi orbitals with a carbocation over three sigma bonds [J].
Lambert, JB ;
Ciro, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :1940-1945
[6]   A REMARKABLE STERIC EFFECT IN PALLADIUM-CATALYZED GRIGNARD COUPLING - REGIOSELECTIVE AND STEREOSELECTIVE MONOALKYLATION AND SELECTIVE ARYLATION OF 1,1-DICHLORO-1-ALKENES [J].
MINATO, A ;
SUZUKI, K ;
TAMAO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1257-1258
[7]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[8]  
Neidlein R, 1998, SYNTHESIS-STUTTGART, P1362
[9]   Stereo- and regiocontrolled synthesis of branched trisubstituted conjugated dienes by palladium(0)-catalyzed cross-coupling reaction [J].
Panek, JS ;
Hu, T .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (15) :4912-4913
[10]   NEW SYNTHESIS OF 1,1-DIBROMOOLEFINS VIA PHOSPHINE-DIBROMOMETHYLENES - REACTION OF TRIPHENYLPHOSPHINE WITH CARBON TETRABROMIDE [J].
RAMIREZ, F ;
MCKELVIE, N ;
DESAI, NB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (09) :1745-&