Organic Chemistry Portal

Abstracts

Search:

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: mcwhite7illinois.edu

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 (free Supporting Information)


Abstract

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.

see article for more examples



Key Words

allylic amines, BQ, oxygen


ID: J48-Y2016