Photocatalytic α-Alkylation of Amines with Alkyl Halides

Lingying Leng, Joseph M. Ready

Research output: Contribution to journalArticlepeer-review

Abstract

α-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 α-amino radical and a stabilized carbon-centered radical (allyl, benzyl, α-carbonyl) followed by radical recombination. This approach offers a mild, atom-economical, redox neutral synthesis of α-branched amines that shows broad scope and avoids pre-metalated reagents.

Original languageEnglish (US)
JournalUnknown Journal
DOIs
StatePublished - Sep 28 2020

Keywords

  • Photocatalysis

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Science(all)

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