Synthesis of Bridged Bicyclic Amines by Intramolecular Amination of Remote C-H Bonds: Synergistic Activation by Light and Heat

Michaelyn C. Lux, Justin Jurczyk, Yu Hong Lam, Zhiguo J. Song, Chao Ma, Jose B. Roque, Jin Su Ham, Nunzio Sciammetta, Donovon Adpressa, Richmond Sarpong, Charles S. Yeung

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The construction of complex aza-cycles is of interest to drug discovery due to the prevalence of nitrogen-containing heterocycles in pharmaceutical agents. Herein we report an intramolecular C-H amination approach to afford value-added and complexity-enriched bridged bicyclic amines. Guided by density functional theory and nuclear magnetic resonance investigations, we determined the unique roles of light and heat activation in the bicyclization mechanism. We applied both light and heat activation in a synergistic fashion, achieving gram-scale bridged aza-cycle synthesis.

Original languageEnglish (US)
Pages (from-to)6578-6583
Number of pages6
JournalOrganic letters
Volume22
Issue number16
DOIs
StatePublished - Aug 21 2020
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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