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Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach

Zheng-Jun Wang, Shuai Zheng, Eugénie Romero, Jennifer K. Matsui, Gary A. Molander*

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States, Email: gmolandrsas.upenn.edu

Z.-J. Wang, S. Zheng, E. Romero, J. K. Matsui, G. A. Molander, Org. Lett., 2019, 21, 6543-6547.

DOI: 10.1021/acs.orglett.9b02473 (free Supporting Information)


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Abstract

Photoredox/nickel dual catalysis enables a radical-mediated functionalization of allyl alcohol (derivatives) with a variety of alkyl 1,4-dihydropyridines with high linear and E-selectivity. This reaction avoids harsh conditions (e.g., strong base, elevated temperature). Additionally, using aryl sulfinate salts as radical precursors, allyl sulfones can also be obtained.

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proposed mechanism



Key Words

allylation, Tsuji-Trost reaction, photochemistry


ID: J54-Y2019