Intermediates of copper(I)-catalyzed C-S cross coupling of thiophenol with aryl halide by in situ ESI-MS study

被引：34

作者：

Cheng, Shao-Wen ^{[1
,2
]}

Tseng, Mei-Chun ^{[1
]}

Lii, Kwang-Hwa ^{[2
]}

Lee, Chi-Rung ^{[3
]}

Shyu, Shin-Guang ^{[1
,2
]}

机构：

[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan

[2] Natl Cent Univ, Dept Chem, Tao Yuan 320, Taiwan

[3] Minghsin Univ Sci & Technol, Dept Chem & Mat Engn, Hsinchu, Taiwan

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 19期

关键词：

SULFUR BOND FORMATION; VERSATILE LIGAND; EFFICIENT; THIOLS; COPPER; IODIDES; ULLMANN; CATALYST; ARYLATION; THIOETHERS;

D O I：

10.1039/c1cc11067e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Complexes [Cu(SPh)(2)](-), [Cu(SPh)I](-) and K[Cu(SPh)(2)(Ph)](+) were observed by in situ electrospray ionization mass spectrometry (ESI-MS) analysis of the copper(I)-catalyzed C-S coupling reaction under catalytic reaction conditions indicating that they are intermediates in the reaction. A catalytic cycle was proposed based on these observations.

引用

页码：5599 / 5601

页数：3

共 39 条

[31] Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols [J].

Sperotto, Elena ;

van Klink, Gerard P. M. ;

de Vries, Johannes G. ;

van Koten, Gerard .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5625-5628

[32] Diamine ligands in copper-catalyzed reactions [J].

Surry, David S. ;

Buchwald, Stephen L. .

CHEMICAL SCIENCE, 2010, 1 (01) :13-31

[33] Mono- or dichalcogenation of aryl iodide with sulfur or selenium by copper catalyst and aluminum [J].

Taniguchi, N .

SYNLETT, 2005, (11) :1687-1690

[34] A general and efficient CuI/BtH catalyzed coupling of aryl halides with thiols [J].

Verma, Akhilesh Kumar ;

Singh, Jaspal ;

Chaudhary, Ritu .

TETRAHEDRON LETTERS, 2007, 48 (40) :7199-7202

[35] Cobalt-catalyzed aryl-sulfur bond formation [J].

Wong, Ying-Chieh ;

Jayanth, Thiruvellore Thatai ;

Cheng, Chien-Hong .

ORGANIC LETTERS, 2006, 8 (24) :5613-5616

[36] A reusable FeCl3•6H2O/cationic 2,2′-bipyridyl catalytic system for the coupling of aryl iodides with thiols in water under aerobic conditions [J].

Wu, Wei-Yi ;

Wang, Jui-Chan ;

Tsai, Fu-Yu .

GREEN CHEMISTRY, 2009, 11 (03) :326-329

[37] Efficient C-S cross coupling catalyzed by Cu2O [J].

Xu, Hua-Jian ;

Zhao, Xiao-Yang ;

Deng, Jin ;

Fu, Yao ;

Feng, Yi-Si .

TETRAHEDRON LETTERS, 2009, 50 (04) :434-437

[38] The first n-heterocyclic carbene-based nickel catalyst for C-S coupling [J].

Zhang, Yugen ;

Ngeow, Kao Chin ;

Ying, Jackie Y. .

ORGANIC LETTERS, 2007, 9 (18) :3495-3498

[39] A mild and efficient copper-catalyzed coupling of aryl iodides and thiols using an oxime-phosphine oxide ligand [J].

Zhu, Di ;

Xu, Lei ;

Wu, Fan ;

Wan, Boshun .

TETRAHEDRON LETTERS, 2006, 47 (32) :5781-5784

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