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

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.

SUBMITTER: Shu XZ

PROVIDER: S-EPMC4333587 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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

Shu Xing-zhong XZ Zhang Miao M He Ying Y Frei Heinz H Toste F Dean FD

Journal of the American Chemical Society 20140414 16

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. ...[more]

PMID: 24730447

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