Regioselective Radical Amino-Functionalizations of Allyl Alcohols via Dual Catalytic Cross-Coupling

Abstract

The regioselective amination and cross-coupling of a range of nucleophiles with allyl alcohols has been enabled by a dual catalytic strategy. This approach entails the combined action of an Ir photocatalyst that enables mild access to N-radicals via an energy transfer mechanism, as well as a Cu complex that intercepts the ensuing alkyl radical upon cyclization. Merger of this Cu-catalyzed cross-coupling enables a broad range of nucleophiles (e.g., CN, SCN, N3, vinyl, allyl) to engage in radical amino-functionalizations of olefins. Notably, stereo, regio, and kinetic probes provide insights into the nature of this Cu-based radical interception.

Topics & Concepts