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

[1] ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES [J].

AUBURN, PR ;

MACKENZIE, PB ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2033-2046

[2] SOME COMPLEXES OF DITERTIARY PHOSPHINES WITH NICKEL(2) AND NICKEL(3) [J].

BOOTH, G ;

CHATT, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAY) :3238-&

[3] SELECTIVE SYNTHESES WITH ORGANOMETALLIC REAGENTS .7. STRUCTURAL DYNAMICS OF PENTADIENYL METAL-COMPOUNDS BEARING A TERMINAL ALKYL SUBSTITUENT - BOTH STEREOSELECTIVE AND STEREODEFENSIVE SYNTHESIS OF A NATURAL PERFUME [J].

BOSSHARDT, H ;

SCHLOSSER, M .

HELVETICA CHIMICA ACTA, 1980, 63 (08) :2393-2403

[4] NEW CATALYTIC SYNTHESIS OF NON-CONJUGATED ALKENYNES [J].

CATELLANI, M ;

CHIUSOLI, GP ;

SALERNO, G ;

DALLATOMASINA, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 146 (03) :C19-C22

[5] ENANTIOSELECTIVE CROSS-COUPLING OF VINYL-ELECTROPHILES, ARYL-ELECTROPHILES AND ALLYL-ELECTROPHILES CATALYZED BY NICKEL-COMPLEXES CONTAINING (R,R)-1,2-CYCLOPENTANEDIYLBIS(DIPHENYLPHOSPHINE) AND RELATED LIGANDS [J].

CONSIGLIO, G ;

INDOLESE, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 417 (1-2) :C36-C40

[6] HIGHLY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES PROMOTED BY CHIRAL OXAZABOROLIDINES [J].

COREY, EJ ;

CIMPRICH, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3151-3152

[7]

DAVIES JA, 1995, COMPREHENSIVE ORGANO, V9, P291

[8]

Godleslcy S., 1991, COMPREHENSIVE ORGANI, V4, P585

[9] CROSS-COUPLING OF TERTIARY ALKYL GRIGNARD-REAGENTS WITH BETA-BROMOSTYRENE CATALYZED BY DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]NICKEL(II) [J].

HAYASHI, T ;

KONISHI, M ;

YOKOTA, K ;

KUMADA, M .

CHEMISTRY LETTERS, 1980, (06) :767-768

[10] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .8. PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC AMINATION [J].

HAYASHI, T ;

YAMAMOTO, A ;

ITO, Y ;

NISHIOKA, E ;

MIURA, H ;

YANAGI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6301-6311

← 1 2 3 →