Nickel-catalyzed allylation of lithium 1-alkynyl(trialkoxy)borates with 1,3-disubstituted allyl carbonates

被引：38

作者：

Chen, H ^{[1
]}

Deng, MZ ^{[1
]}

机构：

[1] Acad Sinica, Shanghai Inst Organ Chem, Organomet Chem Lab, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2000年 / 603卷 / 02期

基金：

中国国家自然科学基金;

关键词：

nickel catalysts; alkynylborates; allyl carbonate; cross-coupling;

D O I：

10.1016/S0022-328X(00)00164-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first Suzuki-type cross-coupling of alkynylborates with 1,3-disubstitued allyl carbonates was studies. It was found that nickel complexes readily catalyzed the reaction giving normal coupling products in good to excellent yields. The nickel complexes of dppe or dppen revealed a higher catalytic activity than that of NiCl2(PPh3)(2) or NiCl2(dppf). This is a substrate-controlled reaction with high regioselectivity. The asymmetric cross-coupling reaction of alkynylborates with allyl carbonate enantioselectively produced an allyl substituted alkyne with 13%ee. (C) 2000 Elsevier Science S.A. All rights reserved.

引用

页码：189 / 193

页数：5

共 29 条

[21]

NORMANT JF, 1972, SYNTH-INT J METHODS, P63

[22]

SEVIN A, 1965, TETRAHEDRON LETT, P1953

[23]

SEVIN A, 1974, B SOC CHIM FR I-PHYS, P913

[24] AN UNPRECEDENTED ELECTRONIC PREFERENCE FOR THE META PRODUCT IN DIELS-ALDER REACTIONS OF ETHYNYLDIALKYLBORANES - [(TRIMETHYLSILYL)ETHYNYL]-9-BBN AS A REACTIVE AND VERSATILE DIENOPHILE [J].

SINGLETON, DA ;

LEUNG, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18) :4796-4797

[25]

TAYET J, 1989, TETRAHEDRON LETT, V30, P2225

[26] NICKEL-CATALYZED COUPLING OF ALLYLAMINES AND BORONIC ACIDS [J].

TROST, BM ;

SPAGNOL, MD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (17) :2083-2096

[27] CHEMISTRY OF DIBENZYLIDENEACETONE-PALLADIUM(0) COMPLEXES .1. NOVEL TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(SOLVENT) COMPLEXES AND THEIR REACTIONS WITH QUINONES [J].

UKAI, T ;

KAWAZURA, H ;

ISHII, Y ;

BONNET, JJ ;

IBERS, JA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 65 (02) :253-266

[28] Coupling reaction of 4-cyclopentene-1,3-diol monoacetate and lithium alkenylborates and its application to chiral synthesis of prostaglandin intermediates [J].

Usmani, SB ;

Takahisa, E ;

Kobayashi, Y .

TETRAHEDRON LETTERS, 1998, 39 (07) :601-604

[29]

ZIEGENBEIN W, 1969, CHEM ACETYLENES, P169

← 1 2 3 →