A synthesis of allylboronates via the palladium(0)-catalyzed cross-coupling reaction of bis(pinacolato)diboron with allylic acetates

被引：126

作者：

Ishiyama, T ^{[1
]}

Ahiko, T ^{[1
]}

Miyaura, N ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC ENGN,DIV MOL CHEM,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 38期

关键词：

D O I：

10.1016/0040-4039(96)01505-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cross-coupling reaction of bis(pinacolato)diboron [(Me(4)C(2)O(2))BB(O(2)C(2)Me(4))] with allyl acetates regio- and E-stereoselectively provided the pinacol esters of allylboronic acids in high yields. The reaction was efficiently catalyzed by Pd(dba)(2) in DMSO at 50 degrees C. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6889 / 6892

页数：4

共 26 条

[1] STUDIES RELATING TO BORON .5. CHEMISTRY OF THE DIBUTYLBORON GROUP [J].

AUTEN, RW ;

KRAUS, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (13) :3398-3401

[2] SYNTHESIS OF ORGANOTRIALKYLSTANNANES - THE REACTION BETWEEN ORGANIC HALIDES AND HEXAALKYLDISTANNANES IN THE PRESENCE OF PALLADIUM COMPLEXES [J].

AZIZIAN, H ;

EABORN, C ;

PIDCOCK, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 215 (01) :49-58

[3]

BUMAGIN NA, 1983, DOKL AKAD NAUK SSSR, V274, P1103

[4] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES [J].

COREY, EJ ;

YU, CM ;

KIM, SS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5495-5496

[5] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].

ECHAVARREN, AM ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486

[6]

Heck R.F., 1985, PALLADIUM REAGENTS O

[7] LIMITED DIASTEREOSELECTIVITY ON ADDITION OF GAMMA-ALKOXY-Z-ALLYLBORONATES TO ALDEHYDES [J].

HOFFMANN, RW ;

KEMPER, B .

TETRAHEDRON LETTERS, 1982, 23 (08) :845-848

[8]

HOFFMANN RW, 1991, LIEBIGS ANN CHEM, P1195

[9]

HOFFMANN RW, 1993, LIEBIGS ANN CHEM, P771

[10] REGIOCHEMICAL AND STEREOCHEMICAL ASPECTS OF THE PALLADIUM-CATALYZED REACTIONS OF SILANES [J].

HORN, KA .

CHEMICAL REVIEWS, 1995, 95 (05) :1317-1350

← 1 2 3 →