Palladium-catalyzed phosphine-, copper-free and aerobic Sonogashira coupling in aqueous media

被引：11

作者：

Liu, Chun ^{[1
]}

Bao, Fanying ^{[1
]}

Ni, Qijian ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China

来源：

ARKIVOC | 2011年

基金：

中国国家自然科学基金;

关键词：

Palladium; phosphine-free; aerobic; Sonogashira coupling; aqueous; N-HETEROCYCLIC CARBENES; ARYL BROMIDES; LIGAND-FREE; EFFICIENT CATALYSTS; COMPLEXES; WATER; SUZUKI; TEMPERATURE; ACETYLENES; CHLORIDES;

D O I：

10.3998/ark.5550190.0012.b06

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, highly efficient and phosphine-free protocol for the Sonogashira coupling of aryl iodides with terminal alkynes has been developed using Pd-2(dba)(3) (dba=dibenzylideneacetone) as the catalyst under aqueous, copper-free and aerobic conditions. The coupling of aryl iodides with aromatic terminal alkynes provided good to excellent yields and moderate to good yields were achieved using aliphatic terminal alkynes as one of the coupling partners. Aqueous ethanol as solvent is economical and environmentally benign in accordance with the concept of green chemistry.

引用

页码：60 / 68

页数：9

共 48 条

[1] Oxime palladacycles:: Stable and efficient catalysts for carbon-carbon coupling reactions [J].

Alonso, DA ;

Nájera, C ;

Pacheco, MC .

ORGANIC LETTERS, 2000, 2 (13) :1823-1826

[2] A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles [J].

Alonso, DA ;

Nájera, C ;

Pacheco, MC .

TETRAHEDRON LETTERS, 2002, 43 (51) :9365-9368

[3] 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

[4] Copper-free Sonogashira coupling reactions catalyzed by a water-soluble Pd-salen complex under aerobic conditions [J].

Bakherad, Mohammad ;

Keivanloo, Ali ;

Bahramian, Bahram ;

Hashemi, Mahdieh .

TETRAHEDRON LETTERS, 2009, 50 (14) :1557-1559

[5] SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES [J].

CASSAR, L .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :253-257

[6] Copper-Free Palladium-Catalyzed Sonogashira Coupling-Annulation: Efficient One-Pot Synthesis of Functionalized Pyrano[4,3-b]quinolines from 2-Chloro-3-formylquinolines [J].

Chandra, Atish ;

Singh, Bhawana ;

Khanna, Ranjana S. ;

Singh, Radhey M. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5664-5666

[7] A copper- and amine-free sonogashira reaction employing aminophosphines as ligands [J].

Cheng, J ;

Sun, YH ;

Wang, F ;

Guo, MJ ;

Xu, JH ;

Pan, Y ;

Zhang, ZG .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5428-5432

[8] The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL REVIEWS, 2007, 107 (03) :874-922

[9] PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES [J].

DIECK, HA ;

HECK, FR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :259-263

[10] Sonogashira cross-coupling reactions catalysed by copper-free palladium zeolites [J].

Djakovitch, L ;

Rollet, P .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1782-1792

← 1 2 3 4 5 →