Palladium-catalyzed cross-coupling reaction of alkynylzincs with benzylic electrophiles

被引：65

作者：

Qian, MX ^{[1
]}

Negishi, EI ^{[1
]}

机构：

[1] Purdue Univ, Herbert C Brown Lab Chem, W Lafayette, IN 47907 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 16期

基金：

美国国家卫生研究院;

关键词：

palladium-catalyzed cross-coupling; alkynylzincs; benzylic electrophiles; benzylated alkynes; Pd(DPEphOS)Cl2-;

D O I：

10.1016/j.tetlet.2005.02.137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of alkynylzinc bromides with benzyl bromides or chlorides in the presence of a catalytic amount of Pd(DPE-phos)Cl-2 in THF at 23 degrees C cleanly produces the corresponding benzylated alkynes in 73-97% yields. With 10(-3) mol% of Pd(DPE-phos)Cl-2, the maximum turnover number of 7.1 x 10(4) has been observed for the formation of PhC CCH2Ph. (c) 2005 Published by Elsevier Ltd.

引用

页码：2927 / 2930

页数：4

共 20 条

[1] Transition metal catalysed cross-coupling between benzylic halides and aryl nucleophiles. Synthesis of some toxicologically interesting tetrachlorobenzyltoluenes. [J].

de Lang, RJ ;

van Hooijdonk, MJCM ;

Brandsma, L ;

Kramer, H ;

Seinen, W .

TETRAHEDRON, 1998, 54 (12) :2953-2966

[2] SYNTHESIS OF 3-SUBSTITUTED FURANS BY DIRECTED LITHIATION AND PALLADIUM CATALYZED COUPLING [J].

ENNIS, DS ;

GILCHRIST, TL .

TETRAHEDRON, 1990, 46 (07) :2623-2632

[3] PALLADIUM-MEDIATED BENZYLATION OF DIMETALLATED 1-BUTYLINDOLE-3-CARBOXYLIC ACID [J].

FISHER, LE ;

LABADIE, SS ;

REUTER, DC ;

CLARK, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6224-6225

[4] DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES [J].

HAYASHI, T ;

KONISHI, M ;

KOBORI, Y ;

KUMADA, M ;

HIGUCHI, T ;

HIROTSU, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) :158-163

[5] NEW DIPHOSPHINE LIGANDS BASED ON HETEROCYCLIC AROMATICS INDUCING VERY HIGH REGIOSELECTIVITY IN RHODIUM-CATALYZED HYDROFORMYLATION - EFFECT OF THE BITE ANGLE [J].

KRANENBURG, M ;

VANDERBURGT, YEM ;

KAMER, PCJ ;

VANLEEUWEN, PWNM ;

GOUBITZ, K ;

FRAANJE, J .

ORGANOMETALLICS, 1995, 14 (06) :3081-3089

[6] C-glycosylated diphenylmethanes and benzophenones:: The Stille coupling reaction of C-glycosylated aryl tins with benzyl bromides and acid chlorides [J].

Kuribayashi, T ;

Gohya, S ;

Mizuno, Y ;

Satoh, S .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1999, 18 (04) :393-401

[7] Tuning of regioselectivity in the coupling reaction involving allenic/propargylic palladium species [J].

Ma, SM ;

Zhang, AB .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2287-2294

[8] Efficient synthesis of 1,1-diaryl 1,2-dienes via Pd(0)-catalyzed coupling of aryl halides with allenic propargylic zinc reagents [J].

Ma, SM ;

Zhang, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9601-9604

[9] PALLADIUM-CATALYZED COUPLING OF TETRAORGANOTIN COMPOUNDS WITH ARYL AND BENZYL HALIDES - SYNTHETIC UTILITY AND MECHANISM [J].

MILSTEIN, D ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4992-4998

[10] Palladium-catalyzed alkynylation [J].

Negishi, E ;

Anastasia, L .

CHEMICAL REVIEWS, 2003, 103 (05) :1979-2017

← 1 2 →