Recyclable Iron/Graphite Catalyst for C-S Cross Coupling of Thiols with Aryl Halides under Ligand-Free Conditions

被引：26

作者：

Akkilagunta, Vijay Kumar ^{[1
]}

Reddy, Vutukuri Prakash ^{[1
]}

Rao, Kakulapati Rama ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500607, Andhra Pradesh, India

来源：

SYNLETT | 2010年 / 08期

关键词：

arylhalides; cross-coupling; recyclable catalyst; iron; thiols; BORONIC ACIDS; PALLADIUM; EFFICIENT; IRON; IODIDES; OXIDE; SUBSTITUTION; THIOETHERS; ARYLATION; GRAPHITE;

D O I：

10.1055/s-0029-1219801

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A recyclable iron/graphite (Fe/Cg) catalyst for the efficient C-S cross-coupling of various iodoarenes with aromatic/aliphatic thiols has been developed under ligand-free conditions (26 examples, up to 99% yield). The catalyst can be easily recovered and recycled up to seven cycles without loss of activity.

引用

页码：1260 / 1264

页数：5

共 47 条

[1] Copper-catalyzed synthesis of vinyl sulfides [J].

Bates, CG ;

Saejueng, P ;

Doherty, MQ ;

Venkataraman, D .

ORGANIC LETTERS, 2004, 6 (26) :5005-5008

[2] A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].

Bates, CG ;

Gujadhur, RK ;

Venkataraman, D .

ORGANIC LETTERS, 2002, 4 (16) :2803-2806

[3] Iron-catalyzed C-O cross-couplings of phenols with aryl iodides [J].

Bistri, Olivia ;

Correa, Arkaitz ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :586-588

[4] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[5] On the Role of Metal Contaminants in Catalyses with FeCl3 [J].

Buchwald, Stephen L. ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587

[6] 1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols [J].

Chen, Yao-Jung ;

Chen, Hsin-Hung .

ORGANIC LETTERS, 2006, 8 (24) :5609-5612

[7] Iron-catalyzed S-arylation of thiols with aryl iodides [J].

Correa, Arkaitz ;

Carril, Monica ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2880-2883

[8] Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes [J].

Correa, Arkaitz ;

Mancheno, Olga Garcia ;

Bolm, Carsten .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (06) :1108-1117

[9] Iron-catalyzed N-arylation of nitrogen nucleophiles [J].

Correa, Arkaitz ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8862-8865

[10] CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands [J].

Deng, W ;

Zou, Y ;

Wang, YF ;

Liu, L ;

Guo, QX .

SYNLETT, 2004, (07) :1254-1258

← 1 2 3 4 5 →