Organic Chemistry Portal

Abstracts

Search:

Di-tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization

Kai Luo, Wen-Chao Yang, Kai Wei, Yue Liu, Jun-Ke Wang and Lei Wu*

*Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China, Email: rickywunjau.edu.cn

K. Luo, W.-C. Yang, K. Wei, Y. Liu, J.-K. Wang, L. Wu, Org. Lett., 2019, 21, 7851-7856.

DOI: 10.1021/acs.orglett.9b02837 (free Supporting Information)


see article for more reactions

Abstract

Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway.

see article for more examples

proposed mechanism



Key Words

benzothiazoles, DTBP


ID: J54-Y2019