Aminoalkylation of Alkenes Enabled by Triple Radical Sorting

William L. Lyon, Johnny Z. Wang, Jesús Alcázar, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

Abstract

The direct synthesis of C(sp3)-rich architectures is a driving force for innovation in synthetic organic chemistry. Such scaffolds impart beneficial properties onto drug molecules that correlate with greater clinical success. Consequently, there is a strong impetus to develop new methods by which to access sp3-rich molecules from commercial feedstocks, such as alkenes. Herein, we report a three-component aminoalkylation reaction that utilizes the principles of triple radical sorting to regioselectively add N-centered and C-centered radicals across alkenes. This process relies upon photoredox catalysis to transform alkyl bromides and reductively activated N-centered radical precursors into high-energy radical species in a redox-neutral fashion. A broad scope of coupling partners is demonstrated, with multiple synthetic applications, including facile syntheses of pharmacophoric substituted N-heterocycles.

Original languageEnglish (US)
Pages (from-to)2296-2302
Number of pages7
JournalJournal of the American Chemical Society
Volume147
Issue number3
DOIs
StatePublished - Jan 22 2025

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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