Nickel-Schiff base complex catalyzed C-S cross-coupling of thiols with organic chlorides

被引：58

作者：

Gogoi, Prasanta ^{[1
]}

Hazarika, Sukanya ^{[1
]}

Sarma, Manas J. ^{[2
]}

Sarma, Kuladip ^{[1
]}

Barman, Pranjit ^{[1
]}

机构：

[1] Natl Inst Technol, Dept Chem, Silchar 788010, Assam, India

[2] Gauhati Univ, Dept Chem, Gauhati 781014, Assam, India

来源：

TETRAHEDRON | 2014年 / 70卷 / 41期

关键词：

Nickel-Schiff base complex; Thiols; Organic chloride; NaOH; BOND FORMATION; ARYL HALIDES; CRYSTAL-STRUCTURE; LIGAND; EFFICIENT; IODIDES; ARYLATION; NI(II); CU(II); CO(II);

D O I：

10.1016/j.tet.2014.08.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an efficient, mild and convenient synthetic protocol for the C-S cross-coupling reaction of various aryl, benzyl, allyl chlorides and thiols using 5 mol % Nickel-Schiff base catalyst with NaOH as the base, in DMF at 70 degrees C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available organic chlorides and thiols. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：7484 / 7489

页数：6

共 42 条

[1] Rapid Ullmann-type synthesis of aryl sulfides using a copper(I) catalyst and ligand under microwave irradiation [J].

Bagley, Mark C. ;

Dix, Matthew C. ;

Fusillo, Vincenzo .

TETRAHEDRON LETTERS, 2009, 50 (26) :3661-3664

[2] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[3] 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

[4] Transition Metal Catalyzed Synthesis of Aryl Sulfides [J].

Eichman, Chad C. ;

Stambuli, James P. .

MOLECULES, 2011, 16 (01) :590-608

[5] Zinc-Mediated Palladium-Catalyzed Formation of Carbon-Sulfur Bonds [J].

Eichman, Chad C. ;

Stambuli, James P. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) :4005-4008

[6] A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols [J].

Fernández-Rodríguez, MA ;

Shen, QL ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2180-2181

[7] A General, Efficient, and Functional-Group-Tolerant Catalyst System for the Palladium-Catalyzed Thioetherification of Aryl Bromides and Iodides [J].

Fernandez-Rodriguez, Manuel A. ;

Hartwig, John F. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04) :1663-1672

[8] One-pot synthesis of aryl alkyl thioethers and diaryl disulfides using carbon disulfide as a sulfur surrogate in the presence of diethylamine catalyzed by copper(I) iodide in polyethylene glycol (PEG200) [J].

Firouzabadi, Habib ;

Iranpoor, Nasser ;

Samadi, Arash .

TETRAHEDRON LETTERS, 2014, 55 (06) :1212-1217

[9] C-S bond formation catalyzed by N-heterocylic carbene palladium phosphine complexes [J].

Fu, Ching-Feng ;

Liu, Yi-Hung ;

Peng, Shei-Ming ;

Liu, Shiuh-Tzung .

TETRAHEDRON, 2010, 66 (12) :2119-2122

[10] An Efficient Protocol for the Carbon-Sulfur Cross-Coupling of Sulfenyl Chlorides with Arylboronic Acids using a Palladium Catalyst [J].

Gogoi, Prasanta ;

Kalita, Mukul ;

Barman, Pranjit .

SYNLETT, 2014, 25 (06) :866-870

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