Lewis Acid-Catalyzed, Copper(II)-Mediated Synthesis of Heteroaryl Thioethers under Base-Free Conditions

被引：171

作者：

Dai, Chao ^{[1
,2
]}

Xu, Zhaoqing ^{[1
]}

Huang, Fei ^{[1
]}

Yu, Zhengkun ^{[1
]}

Gao, Yan-Feng ^{[2
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[2] Zhengzhou Univ, Dept Bioengn, Zhengzhou 450001, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 09期

关键词：

PHASE TRANSFER CATALYSIS; DIRECT ARYLATION; BIOLOGICAL-ACTIVITIES; S-ALKYLATION; FUNCTIONALIZATIONS; HETEROCYCLES; BENZOXAZOLE; DISULFIDES; INHIBITORS; COMPLEXES;

D O I：

10.1021/jo202624s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Lewis acid (Ag-I, Ni-II, or Fe-II) catalyzed, Cu-II-mediated thiolation reaction between heteroarenes and thiols was achieved with good yield under base-free conditions. DMSO could serve as an effective methylthiolation reagent for the synthesis of heterocyclic methyl thioethers.

引用

页码：4414 / 4419

页数：6

共 46 条

[11] SELECTIVE S-ALKYLATION IN PHASE TRANSFER CATALYSIS OF 2-PYRIDINE-THIONE, 2-PYRIMIDINE-THIONE AND BENZOXAZOLE-THIONE [J].

DOU, HJM ;

HASSANALY, P ;

KISTER, J ;

METZGER, J .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1977, 3 (03) :355-358

[12] S-ALKYLATION IN HETEROCYCLIC SERIE BY PHASE TRANSFER CATALYSIS - 2-ALKYLTHIOTHIAZOLES, 2-ALKYLTHIO-DELTA-4-THIAZOLINES AND 2-ALKYLTHIOBENZOTHIAZOLES [J].

DOU, HJM ;

KISTER, J ;

VERNIN, G ;

METZGER, J ;

HASSANALY, P .

HELVETICA CHIMICA ACTA, 1978, 61 (08) :3143-3148

[13]

Eva S., 1999, MOLECULES, V4, P73

[14] Copper-catalyzed direct thiolation of benzoxazole with diaryl disulfides and aryl thiols [J].

Fukuzawa, Shin-ichi ;

Shimizu, Eiji ;

Atsuumi, Yuka ;

Haga, Masatake ;

Ogata, Kenichi .

TETRAHEDRON LETTERS, 2009, 50 (20) :2374-2376

[15] Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAO-A inhibitors:: Biological activities, CoMFA analysis, and active site modeling [J].

Gallardo-Godoy, A ;

Fierro, A ;

McLean, TH ;

Castillo, M ;

Cassels, BK ;

Reyes-Parada, M ;

Nichols, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (07) :2407-2419

[16] Tuning the Regioselectivity of Palladium-Catalyzed Direct Arylation of Azoles by Metal Coordination [J].

Gorelsky, Serge I. .

ORGANOMETALLICS, 2012, 31 (03) :794-797

[17] Copper-Catalyzed Oxidative Amination of Benzoxazoles via C-H and C-N Bond Activation: A New Strategy for Using Tertiary Amines as Nitrogen Group Sources [J].

Guo, Shengmei ;

Chan, Bo ;

Xie, Yinjun ;

Xia, Chungu ;

Huang, Hanmin .

ORGANIC LETTERS, 2011, 13 (03) :522-525

[18] A Highly Efficient Palladium/Copper Cocatalytic System for Direct Arylation of Heteroarenes: An Unexpected Effect of Cu(Xantphos)I [J].

Huang, Jinkun ;

Chan, Johann ;

Chen, Ying ;

Borths, Christopher J. ;

Baucom, Kyle D. ;

Larsen, Robert D. ;

Faul, Margaret M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3674-+

[19] Microwave-assisted, one-pot syntheses and fungicidal activity of polyfluorinated 2-benzylthiobenzothiazoles [J].

Huang, Wei ;

Yang, Guang-Fu .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) :8280-8285

[20] THE ACID-CATALYZED DECOMPOSITION OF DIAZO CARBONYL-COMPOUNDS .2. SYNTHESIS OF 2-HETEROATOM-SUBSTITUTED OR 5-HETEROATOM-SUBSTITUTED OXAZOLES [J].

IBATA, T ;

YAMASHITA, T ;

KASHIUCHI, M ;

NAKANO, S ;

NAKAWA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (09) :2450-2455

← 1 2 3 4 5 →