Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion

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

doi:10.1021/ja500716j

Title: Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion

Journal Article · Mon Apr 14 00:00:00 EDT 2014 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja500716j· OSTI ID:1179599

Shu, Xing-zhong ^[1]; Zhang, Miao ^[2]; He, Ying ^[3]; Frei, Heinz ^[2]; Toste, F. Dean ^[1]

Department of Chemistry, University of California, Berkeley, California 94720, United States; Chemical Sciences Divisions, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720, United States
Physical Biosciences Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720, United States
Department of Chemistry, University of California, Berkeley, California 94720, United States; Chemical Sciences Divisions, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720, United States; Institute of Chemistry and BioMedical Sciences, Nanjing University, Nanjing 210046, P. R. China

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 then proposed on the basis of mechanistic studies, including time-resolved FT-IR spectroscopy.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; National Institutes of Health (NIH)

Grant/Contract Number:: AC02-05CH11231; RO1 GM073932

OSTI ID:: 1179599

Alternate ID(s):: OSTI ID: 1472033; OSTI ID: 1971223

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Vol. 136 Journal Issue: 16; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 342 works

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