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

A Lewis acid (AgI, NiII, or FeII) catalyzed, CuII-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.

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Bibliographic Details
Published in:Journal of organic chemistry 2012-05, Vol.77 (9), p.4414-4419
Main Authors: Dai, Chao, Xu, Zhaoqing, Huang, Fei, Yu, Zhengkun, Gao, Yan-Feng
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Copper - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Lewis Acids - chemistry
Metals - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Sulfides - chemical synthesis
Sulfides - chemistry
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Description
Summary:A Lewis acid (AgI, NiII, or FeII) catalyzed, CuII-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo202624s