Aryne Aminohalogenation Using Protic Amines Enabled by Halogen Transfer.

Org Lett

Department of Chemistry, University of Minnesota─Twin Cities, Minneapolis, Minnesota 55455, United States.

Published: September 2024

AI Article Synopsis

  • Recent research has concentrated on aryne difunctionalization methods, particularly addressing limitations with nucleophiles and proton sources.
  • The study introduces halogen transfer reagents that facilitate the use of protic amines in aryne aminohalogenation, achieving yields up to 86%.
  • The method showcases versatility with different N-heterocyclic scaffolds and demonstrates the synthetic applications of the resulting products through various derivatizations.

Article Abstract

Methods for aryne difunctionalization have been the focus of recent research, but one limitation is the use of nucleophiles with proton sources. Herein, we demonstrate the use of halogen transfer reagents to enable protic amines in aryne aminohalogenation difunctionalizations in up to 86% yield. This method uses amines and arynes with a variety of N-heterocyclic scaffolds. Through a variety of derivatizations, the synthetic utility of these products is demonstrated.

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Source
http://dx.doi.org/10.1021/acs.orglett.4c02407DOI Listing

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