An efficient water-soluble surfactant-type palladium catalyst for Suzuki cross-coupling reactions in pure water at room temperature

被引：20

作者：

Qiu, Pei ^{[1
]}

Zhao, Jing Yang ^{[1
]}

Shi, Xu ^{[1
]}

Duan, Xin Hong ^{[2
]}

机构：

[1] Beijing Forestry Univ, Coll Mat Sci & Technol, Beijing 100083, Peoples R China

[2] Beijing Forestry Univ, Coll Sci, Beijing 100083, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2016年 / 40卷 / 08期

关键词：

AQUEOUS-MEDIA; GREEN CHEMISTRY; ARYL CHLORIDES; ORGANIC-REACTIONS; MIYAURA; COMPLEXES; LIGANDS; ALKYLPHOSPHINES; ACTIVATION; BROMIDES;

D O I：

10.1039/c6nj00377j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium catalyst based on a bidentate phosphine-type zwitterionic surfactant as a ligand exhibited an excellent catalytic activity in the Suzuki-Miyaura cross coupling reactions. This novel method allowed the reaction of aryl halides with arylboronic acids to occur in pure water at room temperature, forming a variety of biaryls in good to high yields. Heterobiaryls were also efficiently assembled even in the presence of water-insoluble heteroaryl halides as substrates. In addition, such a coupling protocol was successfully used in the iterative diarylation of 2,5-dibromopyridine in one-pot.

引用

页码：6568 / 6572

页数：5

共 55 条

[1] General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].

Anderson, KW ;

Buchwald, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177

[2] Efficient, Selective, and Recyclable Palladium Catalysts in Carbon-Carbon Coupling Reactions [J].

Arpad Molnar .

CHEMICAL REVIEWS, 2011, 111 (03) :2251-2320

[3] Characterization of mutations in the membrane-anchored subunits AaSDHC and AaSDHD of succinate dehydrogenase from Alternaria alternata isolates conferring field resistance to the fungicide boscalid [J].

Avenot, H. ;

Sellam, A. ;

Michailides, T. .

PLANT PATHOLOGY, 2009, 58 (06) :1134-1143

[4] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds [J].

Billingsley, Kelvin L. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) :3484-3488

[5] MCM-41-supported bidentate phosphine palladium(0) complex as an efficient catalyst for the heterogeneous Suzuki reaction [J].

Cai, Mingzhong ;

Sha, Junchao ;

Xu, Qiuhua .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 268 (1-2) :82-86

[6] PALLADIUM-CATALYZED ALKYLATIONS IN AQUEOUS-MEDIA [J].

CASALNUOVO, AL ;

CALABRESE, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4324-4330

[7] Organic Synthesis "On Water" [J].

Chanda, Arani ;

Fokin, Valery V. .

CHEMICAL REVIEWS, 2009, 109 (02) :725-748

[8] Recent Advances in the Palladium Catalyzed Suzuki-Miyaura Cross-Coupling Reaction in Water [J].

Chatterjee, Anamitra ;

Ward, Thomas R. .

CATALYSIS LETTERS, 2016, 146 (04) :820-840

[9] Generation of 3-pyridyl biaryl systems via palladium-catalyzed Suzuki cross-couplings of aryl halides with 3-pyridylboroxin [J].

Cioffi, CL ;

Spencer, WT ;

Richards, JJ ;

Herr, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :2210-2212

[10] Green chemistry: today (and tomorrow) [J].

Clark, JH .

GREEN CHEMISTRY, 2006, 8 (01) :17-21

← 1 2 3 4 5 6 →