Aryne Aminohalogenation Using Protic Amines Enabled by Halogen Transfer

Joshua T. Gavin; Lars W. Anderson; Courtney C. Roberts

doi:10.1021/acs.orglett.4c02407

Aryne Aminohalogenation Using Protic Amines Enabled by Halogen Transfer

Joshua T. Gavin, Lars W. Anderson, Courtney C. Roberts

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	7530-7534
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	36
DOIs	https://doi.org/10.1021/acs.orglett.4c02407
State	Published - Sep 13 2024

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© 2024 American Chemical Society.

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AB - 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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Aryne Aminohalogenation Using Protic Amines Enabled by Halogen Transfer

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