Direct methyl C(sp3)–H azolation of thioanisoles via oxidative radical coupling

Xin Wang; Changhao Li; Yixiao Zhang; Bing Zhang; Kai Sun

doi:10.1039/C9OB01530B

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Direct methyl C(sp³)–H azolation of thioanisoles via oxidative radical coupling†

Xin Wang,^ab Changhao Li,^a Yixiao Zhang,^a Bing Zhang

^b and Kai Sun

*^a

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* Corresponding authors

^a College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455000, P. R. China
E-mail: sunk468@nenu.edu.cn

^b College of Chemistry and Energy, Zhengzhou University, Zhengzhou 450001, P. R. China

Abstract

A method for metal-free, 1,3-dibromo-5,5-dimethylhydantoin mediated methyl C(sp³)–H bond azolation of thioanisoles has been developed, affording a facile route for the construction of nitrogen-functionalized thioanisoles, possibly via a nitrogen-centered radical process. This reaction represents an important addition to the limited number of existing methods for the methyl C(sp³)–H bond functionalization of thioanisoles, and may find practical application in the synthesis of nitrogen-alkylated azoles.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB01530B
Article type: Communication
Submitted: 10 Jul 2019
Accepted: 15 Aug 2019
First published: 15 Aug 2019

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Org. Biomol. Chem., 2019,17, 8364-8368

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Direct methyl C(sp³)–H azolation of thioanisoles via oxidative radical coupling

X. Wang, C. Li, Y. Zhang, B. Zhang and K. Sun, Org. Biomol. Chem., 2019, 17, 8364 DOI: 10.1039/C9OB01530B

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Organic & Biomolecular Chemistry