Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy₂NMe and Water

Rui Wang, Mengyue Ma, Xu Gong, Grace B. Panetti, Xinyuan Fan* and Patrick J. Walsh*

*Nanjing Tech University, Nanjing, 211816, People's Republic of China; University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States, Email: xinyuanfanpku.edu.cn, pwalshsas.upenn.edu

R. Wang, M. Ma, X. Gong, G. B. Panetti, X. Fan, P. J. Walsh, Org. Lett., 2018, 20, 2403-2406.

DOI: 10.1021/acs.orglett.8b00778

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Abstract

Photoredox catalysis mediates an umpolung reactivity of imines exemplified by proton abstraction from water as a key step in the reduction of benzophenone ketimines to amines in very good yields. Deuterium is introduced into amines efficiently using D₂O as an inexpensive deuterium source.

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Key Words

reduction of imines, photochemistry

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ID: J54-Y2018