Photocatalytic Generation of 2‑Azolyl Radicals: Intermediates for the Azolylation of Arenes and Heteroarenes via C–H Functionalization

The 2-azolyl radical, generated from 2-bromoazoles via photocatalysis, is a powerful intermediate for the intermolecular arylation of unmodified (hetero)­arenes. The reaction is characterized by mild conditions, operational simplicity, tolerance toward functional and sterically demanding groups, bro...

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Bibliographic Details
Published in:Organic letters 2016-08, Vol.18 (16), p.3996-3999
Main Authors: Arora, Amandeep, Weaver, Jimmie D
Format: Article
Language:English
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Summary:The 2-azolyl radical, generated from 2-bromoazoles via photocatalysis, is a powerful intermediate for the intermolecular arylation of unmodified (hetero)­arenes. The reaction is characterized by mild conditions, operational simplicity, tolerance toward functional and sterically demanding groups, broad scope, and anti-Minisci selectivity. A working mechanism is provided, and a low-solubility amine is essential for successful coupling. The utility of the reaction is demonstrated via late-stage functionalization of methyl estrone and application toward other bromoarenes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01718