Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling

Patricia Zhang, Chi “Chip” Le and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States, Email: dmacmillprinceton.edu

P. Zhang, C. Le, D. W. C. MacMillan, J. Am. Chem. Soc., 2016, 138, 8084-8087.

DOI: 10.1021/jacs.6b04818

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Abstract

Alkyl bromides can be coupled with aryl or heteroaryl bromides in excellent yields in the presence of commercially available tris(trimethylsilyl)silane and a metallaphotoredox catalyst. It is hypothesized that a photocatalytically generated silyl radical species can perform halogen-atom abstraction to activate alkyl halides as nucleophilic cross-coupling partners.

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Key Words

cross coupling, TTMSS

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ID: J48-Y2016