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Aerobic Linear Allylic C-H Amination: Overcoming Benzoquinone Inhibition

Christopher C. Pattillo, Iulia I. Strambeanu, Pilar Calleja, Nicolaas A. Vermeulen, Tomokazu Mizuno and M. Christina White*

*Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States, Email:

C. P. Pattillo, I. I. Strambeanu, P. Calleja, N. A. Vermeulen, T. Mizuno, M. C. White, J. Am. Chem. Soc., 2016, 138, 1265-1272.

DOI: 10.1021/jacs.5b11294


An efficient aerobic linear allylic C-H amination under palladium(II)/bis-sulfoxide/Brønsted base catalysis operates under operationally simple conditions (1 equiv of olefin, 1 atm O2 or air) with reduced catalyst loadings while providing higher turnovers and product yields than systems employing stoichiometric benzoquinone (BQ) as the terminal oxidant.

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Key Words

allylic amines, BQ, oxygen

ID: J48-Y2016