Photocatalytic α-Alkylation of Amines with Alkyl Halides

29 September 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


a-Branched amines represent essential building blocks for organic synthesis. They are traditionally prepared through nucleophilic addition to imines. These methods often require highly reactive organometallic reagents and proceed under rigorous air- and moisture-free conditions. Here we describe an alternative approach that involves a net dehydrogenative coupling between alkyl bromides and amines. Mechanistically, the reaction likely involves photocatalytic generation of an a-amino radical and a stabilized carbon-centered radical (allyl, benzyl, a-carbonyl) followed by radical recombination. This approach offers a mild, atom-economical, redox neutral synthesis of a-branched amines that shows broad scope and avoids pre-metalated reagents.




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