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Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light

Author:
Liu, Peng, Liu, Wenbo, Li, Chao-Jun
Source:
Journal of the American Chemical Society 2017 v.139 no.40 pp. 14315-14321
ISSN:
1520-5126
Subject:
alkylation, aromatic hydrocarbons, free radicals, moieties, protocols
Abstract:
The Minisci alkylation is useful to functionalize aromatics via alkyl radical addition. Current approaches to prepare alkyl radicals follow either oxidative or reductive pathways from various functional groups. Developing new strategy beyond these traditional methods remains elusive yet highly significant. In this article, we present a redox-neutral and catalyst-free protocol to engender alkyl radicals in the context of trifluoromethylation and general alkylation of arenes. This protocol, via the Norrish type I concept to produce alkyl radicals, accommodates various functional groups and delivers the product in good yields. This method identified a series of compounds as the trifluoromethylation and alkylation reagents assisted by light. It is expected that these compounds can find potential applications in other radical-involved reactions.
Agid:
5833261