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Manganese-Catalyzed N-Alkylation of Sulfonamides Using Alcohols

Benjamin G. Reed-Berendt, Louis C. Morrill*

*Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, U.K., Email: morrilllccardiff.ac.uk

B. G. Reed-Berendt, L. C. Morrill, J. Org. Chem., 2019, 84, 3715-3724.

DOI: 10.1021/acs.joc.9b00203 (free Supporting Information)


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Abstract

A borrowing hydrogen approach using a well-defined and bench-stable Mn(I) PNP pincer precatalyst enables an efficient manganese-catalyzed N-alkylation of sulfonamides with benzylic and simple primary aliphatic alcohols as alkylating agents. A diverse range of aryl and alkyl sulfonamides undergoes mono-N-alkylation in excellent yields.


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proposed mechanism



Key Words

protected primary amines, sulfonamides, p-toluenesulfonamides


ID: J42-Y2019