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Dual visible light photoredox and gold-catalyzed arylative ring expansion.

  • Author(s): Shu, Xing-zhong;
  • Zhang, Miao;
  • He, Ying;
  • Frei, Heinz;
  • Toste, F Dean
  • et al.

Published Web Location

https://doi.org/10.1021/ja500716j
Abstract

A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion-oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts. A mechanism involving generation of an electrophilic gold(III)-aryl intermediate is proposed on the basis of mechanistic studies, including time-resolved FT-IR spectroscopy.

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