Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion

Xing-zhong Shu, Miao Zhang, Ying He, Heinz Frei* and F. Dean Toste*

*Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720; University of California, Berkeley, California 94720, United States, Email: hmfreilbl.gov, fdtosteberkeley.edu

X.-Z. Shu, M. Zhang, Y. He, H. Frei, F. D. Toste, J. Am. Chem. Soc., 2014, 136, 5844-5847.

DOI: 10.1021/ja500716j

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Abstract

A combination of visible light photocatalysis and gold catalysis provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts via ring expansion-oxidative arylation. A mechanism involving generation of an electrophilic gold(III)-aryl intermediate is proposed.

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Key Words

cyclopentanones, ring expansions

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ID: J48-Y2014