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Copper-Catalyzed Intramolecular N-S Bond Formation by Oxidative Dehydrogenative Cyclization

Zhen Wang, Yoichiro Kuninobu* and Motomu Kanai*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: kuninobumol.f.u-tokyo.ac.jp, kanaimol.f.u-tokyo.ac.jp

Z. Wang, Y. Kuninobu, M. Kanai, J. Org. Chem., 2013, 78, 7337-7342.

DOI: 10.1021/jo401056g (free Supporting Information)


Abstract

In a copper-catalyzed synthesis of benzo[d]isothiazol-3(2H)-ones and N-acyl-benzothiazetidine by intramolecular dehydrogenative cyclization, a new nitrogen-sulfur bond is formed by N-H/S-H coupling. The present reaction tolerates various functional groups and gives products in gram scale.

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Key Words

benzo-fused N-Heterocycles, benzo-fused S-heterocycles, Oxygen


ID: J42-Y2013