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Excited-state palladium-catalysed reductive alkylation of imines: scope and mechanism
Authors:Rajesh Kancherla  Krishnamoorthy Muralirajan  Magnus Rueping
Affiliation:KAUST Catalysis Center, KCC, King Abdullah University of Science and Technology, KAUST, Thuwal 23955-6900 Saudi Arabia,
Abstract:
Palladium catalysis induced by visible-light irradiation is a promising tool for promoting unusual chemical transformations. We describe the development of excited-state palladium-catalyzed reductive alkylation of imines with alkyl bromides. The new methodology shows broad functional group tolerance and can additionally be applied in the direct three-component reaction of aldehydes, anilines, and alkyl bromides to give the alkyl amines under mild reaction conditions. Time-resolved photoluminescence experiments allowed the determination of the excited-state reaction kinetics and indicate that the reaction is proceeding via the inner-sphere electron transfer mechanism.

Palladium catalysis induced by visible-light irradiation is a promising tool for promoting unusual chemical reactivity. Here, the hybrid alkyl radical/Pd(i) species generated is used to promote the reductive alkylation of imines.
Keywords:
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