Palladium-catalyzed Suzuki-Miyaura coupling with aryl and heteroaryl bromides using N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine

被引：17

作者：

Wang, Kun ^{[1
]}

Yi, Tao ^{[1
]}

Yu, Xiaojun ^{[1
]}

Zheng, Xueli ^{[1
]}

Fu, Haiyan ^{[1
]}

Chen, Hua ^{[1
]}

Li, Ruixiang ^{[1
]}

机构：

[1] Sichuan Univ, Dept Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2012年 / 26卷 / 07期

关键词：

Suzuki-Miyaura coupling; palladium; tetraphosphine; HIGHLY EFFICIENT CATALYST; ARYLBORONIC ACIDS; HECK CATALYSIS; BORONIC ACIDS; COMPLEXES; TETRAPHOSPHINE; LIGAND; PHOSPHINE; HALIDES; SYSTEM;

D O I：

10.1002/aoc.2869

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An easily prepared tetraphosphine N,N,N',N'-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine (1) combined with PdCl2 affords an efficient catalytic system for Suzuki cross-coupling of aryl and heteroaryl bromides. A high turnover number of 750 000 is obtained with the catalyst loading as low as 1?ppm. This catalyst system exhibits good stability and longevity. In this study, a broad scope of substrates is investigated and satisfactory yields are obtained. Copyright (c) 2012 John Wiley & Sons, Ltd.

引用

收藏

页码：342 / 346

页数：5

相关论文

共 56 条

[1] Novel class of tertiary phosphine ligands based on a phospha-adamantane framework and use in the Suzuki cross-coupling reactions of aryl halides under mild conditions [J].

Adjabeng, G ;

Brenstrum, T ;

Wilson, J ;

Frampton, C ;

Robertson, A ;

Hillhouse, J ;

McNulty, J ;

Capretta, A .

ORGANIC LETTERS, 2003, 5 (06) :953-955

[2] Orthopalladated triaryl phosphite complexes as highly active catalysts in biaryl coupling reactions [J].

Albisson, DA ;

Bedford, RB ;

Lawrence, SE ;

Scully, PN .

CHEMICAL COMMUNICATIONS, 1998, (19) :2095-2096

[3] Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling [J].

Andrus, MB ;

Song, C .

ORGANIC LETTERS, 2001, 3 (23) :3761-3764

[4] PREPARATION AND STRUCTURAL CHARACTERIZATION OF RHODIUM AND PALLADIUM COMPLEXES OF MIXED PHOSPHINE AMINE LIGANDS WITH METHYLENE SPACERS BETWEEN DONOR ATOMS [J].

BALCH, AL ;

OLMSTEAD, MM ;

ROWLEY, SP .

INORGANICA CHIMICA ACTA, 1990, 168 (02) :255-264

[5] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[6] Palladacycles in catalysis - a critical survey [J].

Beletskaya, IP ;

Cheprakov, AV .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :4055-4082

[7] Mechanistic studies of SCS-Pd complexes used in Heck catalysis [J].

Bergbreiter, DE ;

Osburn, PL ;

Frels, JD .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (01) :172-184

[8] New structurally rigid palladium catalysts for the alternating copolymerization of carbon monoxide and ethene [J].

Bianchini, C ;

Lee, HM ;

Meli, A ;

Oberhauser, W ;

Vizza, F ;

Brüggeller, P ;

Rainer, HB ;

Langes, C .

CHEMICAL COMMUNICATIONS, 2000, (09) :777-778

[9] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].

Billingsley, Kelvin ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366

[10] Dichloro-Bis(aminophosphine) Complexes of Palladium: Highly Convenient, Reliable and Extremely Active Suzuki-Miyaura Catalysts with Excellent Functional Group Tolerance [J].

Bolliger, Jeanne L. ;

Frech, Christian M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (13) :4075-4081

← 1 2 3 4 5 6 →