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photochemical alpha alkylation of amines.pdf (1.38 MB)

Photocatalytic α-Alkylation of Amines with Alkyl Halides

preprint
submitted on 28.09.2020 and posted on 29.09.2020 by Lingying Leng, Joseph Ready
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.

History

Email Address of Submitting Author

joseph.ready@utsouthwestern.edu

Institution

UT Southwestern

Country

United States

ORCID For Submitting Author

0000-0003-1305-9581

Declaration of Conflict of Interest

no conflict of interest

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