Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


see article for more reactions

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.

see article for more examples



Key Words

cross coupling, TTMSS


ID: J48-Y2016