Zn-Mediated, Pd-Catalyzed Cross-Couplings in Water at Room Temperature Without Prior Formation of Organozinc Reagents

被引：219

作者：

Krasovskiy, Arkady ^{[1
]}

Duplais, Christophe ^{[1
]}

Lipshutz, Bruce H. ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 43期

关键词：

AQUEOUS-MEDIA; CONJUGATE ADDITIONS; CARBONYL-COMPOUNDS; ORGANIC-SYNTHESIS; ZINC; ULTRASOUND; PALLADIUM; REACTIVITY; HALOARYLS; HALIDES;

D O I：

10.1021/ja906803t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Mix in water, stir. That is all that is required in this new approach to sp(3)-sp(2) cross-couplings between an alkyl iodide and an aryl bromide, both potentially bearing functionality. They react under catalysis by Pd(0) in the presence of zinc powder, aided by a nonionic amphiphile, to give the alkylated aromatic. No organic solvents and no heating; just add water.

引用

页码：15592 / +

页数：3

共 24 条

[1]

[Anonymous], HDB FUNCTIONALIZED O

[2]

[Anonymous], HDB ORGANOPALLADIUM

[3] Bis(μ-oxo)dicopper(III) complexes of a homologous series of simple peralkylated 1,2-diamines:: Steric modulation of structure, stability, and reactivity [J].

Cole, AP ;

Mahadevan, V ;

Mirica, LM ;

Ottenwaelder, X ;

Stack, TDP .

INORGANIC CHEMISTRY, 2005, 44 (21) :7345-7364

[4] Domino Iron Catalysis: Direct Aryl-Alkyl Cross-Coupling [J].

Czaplik, Waldemar Maximilian ;

Mayer, Matthias ;

Jacobi von Wangelin, Axel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :607-610

[5] SELECTIVE ALLYLATION OF CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA [J].

EINHORN, C ;

LUCHE, JL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 322 (02) :177-183

[6] Alkenenitriles: Conjugate additions of alkyl iodides with a silica-supported zinc-copper matrix in water [J].

Fleming, Fraser F. ;

Gudipati, Subrahmanyam ;

Aitken, Jennifer A. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18) :6961-6969

[7]

KHAN NM, 2006, MICELLAR CATALYSIS

[8] ALCOHOLS AS SOLVENT FOR GENERATION AND REACTION OF ALLYLIC ZINC HALIDES WITH ALDEHYDES AND KETONES [J].

KILLINGER, TA ;

BOUGHTON, NA ;

RUNGE, TA ;

WOLINSKY, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 124 (02) :131-134

[9] ULTRASOUND-PROMOTED SELECTIVE PERFLUOROALKYLATION ON THE DESIRED POSITION OF ORGANIC-MOLECULES [J].

KITAZUME, T ;

ISHIKAWA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) :5186-5191

[10] Activation of organozinc reagents with t-Bu-P4 base for transition metal-free catalytic SN2′ reaction [J].

Kobayashi, Koji ;

Ueno, Masahiro ;

Naka, Hiroshi ;

Kondo, Yoshinori .

CHEMICAL COMMUNICATIONS, 2008, (32) :3780-3782

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