TBHP-mediated oxidative thiolation of an sp3 C–H bond adjacent to a nitrogen atom in an amide

Ri-Yuan Tang; Ye-Xiang Xie; Yi-Li Xie; Jian-Nan Xiang; Jin-Heng Li

doi:10.1039/C1CC15397H

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TBHP-mediated oxidative thiolation of an sp³ C–H bond adjacent to a nitrogen atom in an amide†

Ri-Yuan Tang,^ab Ye-Xiang Xie,^a Yi-Li Xie,^b Jian-Nan Xiang*^a and Jin-Heng Li*^a

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* Corresponding authors

^a State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
E-mail: jhli@hnu.edu.cn, jnxiang@hnu.cn
Fax: 0086731 8887 2531
Tel: 0086731 8887 2576

^b College of Chemistry and Materials engineering, Wenzhou University, Wenzhou, China

Abstract

The first example of molecular sieve-promoted TBHP-mediated direct oxidative thiolation of an sp³ C–H bond adjacent to a nitrogen atom with disulfides under metal-free conditions, which allows for preparation of numerous S,N-containing compounds, is presented. Moreover, diverse benzothiazoles and a fipronil analog can be synthesized through this strategy.

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Article information

DOI: https://doi.org/10.1039/C1CC15397H
Article type: Communication
Submitted: 30 Aug 2011
Accepted: 14 Oct 2011
First published: 31 Oct 2011

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Chem. Commun., 2011,47, 12867-12869

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TBHP-mediated oxidative thiolation of an sp³ C–H bond adjacent to a nitrogen atom in an amide

R. Tang, Y. Xie, Y. Xie, J. Xiang and J. Li, Chem. Commun., 2011, 47, 12867 DOI: 10.1039/C1CC15397H

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Chemical Communications