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Simple and Versatile Catalytic System for N-Alkylation of Sulfonamides with Various Alcohols

Mingwen Zhu, Ken-ichi Fujita* and Ryohei Yamaguchi*

*Graduate School of Human and Environmental Studies and Graduate School of Global Environmental Studies, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan, Email: fujitakkagaku.mbox.media.kyoto-u.ac.jp, yamakagaku.mbox.media.kyoto-u.ac.jp

M. Zhu, K.-i. Fujita, R. Yamaguchi, Org. Lett., 2010, 12, 1336-1339.

DOI: 10.1021/ol1002434

Abstract

A low catalyst loading of [Cp*IrCl2]2 in the presence of t-BuOK enables a simple and versatile N-alkylation of sulfonamides with various alcohols based on a catalytic hydrogen transfer reaction. Various N-alkylated sulfonamides were prepared in good to excellent yields. Key catalytic species is a sulfonylimido-bridged unsaturated diiridium complex [(Cp*Ir)2(μ-NTs)2].

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Key Words

sulfonamides

ID: J54-Y2010-0810