Cross-coupling reaction of organoboron compounds via base-assisted transmetalation to palladium(II) complexes

被引:270
作者
Miyaura, N [1 ]
机构
[1] Hokkaido Univ, Dept Mol Chem, Fac Engn, Grad Sch Engn, Sapporo, Hokkaido 0608628, Japan
关键词
cross-coupling; organoboron compounds; palladium(II) complexes;
D O I
10.1016/S0022-328X(02)01264-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Until recently, organoboronic acids have been of limited use in organic synthesis due to their low reactivity for ionic reactions. During the past two decades; however, it has become increasingly clear that they are valuable reagents capable of undergoing many carbon-carbon bond formations in organic syntheses. In 1979, catalytic carbon-carbon bond formation, via transmetalation between organoboron compounds and palladium(II) halides, was found to proceed in the presence of a base. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:54 / 57
页数:4
相关论文
共 52 条
[1]   A sequence of palladium-catalyzed borylation of allyl acetates with bis(pinacolato)diboron and intramolecular allylboration for the cyclization of oxo-2-alkenyl acetates [J].
Ahiko, TA ;
Ishiyama, T ;
Miyaura, N .
CHEMISTRY LETTERS, 1997, (08) :811-812
[2]  
BUCHWALD SL, 2000, STREM CHEMIKER, V1, P1
[3]   Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes [J].
Bumagin, NA ;
Korolev, DN .
TETRAHEDRON LETTERS, 1999, 40 (15) :3057-3060
[4]   Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl- or alkenyltrifluoroborates catalyzed by palladium [J].
Darses, S ;
Genet, JP ;
Brayer, JL ;
Demoute, JP .
TETRAHEDRON LETTERS, 1997, 38 (25) :4393-4396
[5]   Cross-coupling of arenediazonium tetrafluoroborates with arylboronic acids catalysed by palladium [J].
Darses, S ;
Jeffery, T ;
Genet, JP ;
Brayer, JL ;
Demoute, JP .
TETRAHEDRON LETTERS, 1996, 37 (22) :3857-3860
[6]   PALLADIUM-CATALYZED CONJUGATED DIENE SYNTHESIS FROM VINYLIC HALIDES AND OLEFINIC COMPOUNDS [J].
DIECK, HA ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (08) :1083-1090
[7]   A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids [J].
Haddach, M ;
McCarthy, JR .
TETRAHEDRON LETTERS, 1999, 40 (16) :3109-3112
[8]   Transition metal-boryl compounds: Synthesis, reactivity, and structure [J].
Irvine, GJ ;
Lesley, MJG ;
Marder, TB ;
Norman, NC ;
Rice, CR ;
Robins, EG ;
Roper, WR ;
Whittell, GR ;
Wright, LJ .
CHEMICAL REVIEWS, 1998, 98 (08) :2685-2722
[9]   A synthesis of allylboronates via the palladium(0)-catalyzed cross-coupling reaction of bis(pinacolato)diboron with allylic acetates [J].
Ishiyama, T ;
Ahiko, T ;
Miyaura, N .
TETRAHEDRON LETTERS, 1996, 37 (38) :6889-6892
[10]   Synthesis of arylboronates via the palladium(O)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates [J].
Ishiyama, T ;
Itoh, Y ;
Kitano, T ;
Miyaura, N .
TETRAHEDRON LETTERS, 1997, 38 (19) :3447-3450