Allylation of aldehydes via Umpolung of π-allylpalladium(II) with triethylborane

被引:38
作者
Kimura, M [1 ]
Kiyama, I [1 ]
Tomizawa, T [1 ]
Horino, Y [1 ]
Tanaka, S [1 ]
Tamaru, Y [1 ]
机构
[1] Nagasaki Univ, Fac Engn, Dept Appl Chem, Nagasaki 8528521, Japan
关键词
aldehydes; allylation; boron; boron compounds; palladium; palladium compounds;
D O I
10.1016/S0040-4039(99)01359-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Triethylborane induces allylic substrates (benzoates, phenyl ethers, benzyl ethers, but not halides) to undergo allylation of aldehydes in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) The reaction proceeds via Umpolung of pi-allylpalladium. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6795 / 6798
页数:4
相关论文
共 14 条
[1]   PALLADIUM-CATALYZED IMINOCARBONYLATIVE CROSS-COUPLING REACTION BETWEEN HALOARENES, T-BUNC, AND 9-ALKYL-9-BBN DERIVATIVES - SYNTHESIS OF ALKYL ARYL KETONES [J].
ISHIYAMA, T ;
OHE, T ;
MIYAURA, N ;
SUZUKI, A .
TETRAHEDRON LETTERS, 1992, 33 (31) :4465-4468
[2]   SYNTHESIS OF KETONES FROM IODOALKENES, CARBON-MONOXIDE AND 9-ALKYL-9-BORABICYCLO[3,3,1]NONANE DERIVATIVES VIA A RADICAL CYCLIZATION AND PALLADIUM-CATALYZED CARBONYLATIVE CROSS-COUPLING SEQUENCE [J].
ISHIYAMA, T ;
MURATA, M ;
SUZUKI, A ;
MIYAURA, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (03) :295-296
[3]   Novel and highly regio- and stereoselective nickel-catalyzed homoallylation of benzaldehyde with 1,3-dienes [J].
Kimura, M ;
Ezoe, A ;
Shibata, K ;
Tamaru, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4033-4034
[4]   Novel carbonyl-dependent regioselective allylation via diethylzinc-mediated umpolung of π-allylpalladium [J].
Kimura, M ;
Ogawa, Y ;
Shimizu, M ;
Sueishi, M ;
Tanaka, S ;
Tamaru, Y .
TETRAHEDRON LETTERS, 1998, 39 (38) :6903-6906
[5]   Tandem Suzuki cross-coupling-Heck reactions [J].
Kojima, A ;
Honzawa, S ;
Boden, CDJ ;
Shibasaki, M .
TETRAHEDRON LETTERS, 1997, 38 (19) :3455-3458
[6]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[7]  
Miyaura N, 1998, ADV MET ORG, V6, P187
[8]   Unique regio- and stereoselectivity in the allylation of benzaldehyde with 2-substituted allylzincs generated by umpolung of π-allylpalladium [J].
Shimizu, M ;
Kimura, M ;
Tanaka, S ;
Tamaru, Y .
TETRAHEDRON LETTERS, 1998, 39 (07) :609-612
[9]   Propargylation of carbonyl compounds by umpolung of propargylpalladium complexes with diethylzinc [J].
Tamaru, Y ;
Goto, S ;
Tanaka, A ;
Shimizu, M ;
Kimura, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (08) :878-880
[10]   HIGHLY STEREOSELECTIVE ALLYLATION OF BENZALDEHYDE - GENERATION OF A STEREOCHEMICALLY DEFINED ALLYLZINC SPECIES FROM A PI-ALLYLPALLADIUM INTERMEDIATE AND DIETHYLZINC [J].
TAMARU, Y ;
TANAKA, A ;
YASUI, K ;
GOTO, S ;
TANAKA, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :787-789