Title
Visible-Light-Promoted Remote C-H Functionalization of o-Diazoniaphenyl Alkyl Sulfones
Document Type
Article
Publication Date
10-20-2017
Abstract
Visible-light irradiation of ortho-diazoniaphenyl alkyl sulfones in the presence of Ru(bpy) results in remote Csp-H functionalization. Key mechanistic steps in these processes involve intramolecular hydrogen atom transfer from Csp-H bonds to aryl radicals to generate alkyl/benzyl radicals. Subsequent polar crossover occurs by single-electron oxidation of the alkyl/benzyl radicals to carbenium ions that then intercept nucleophiles. We have developed remote hydroxylations, etherifications, an amidation, and C-C bond formation processes using this strategy.
Publication Source (Journal or Book title)
Organic letters
First Page
5553
Last Page
5556
Recommended Citation
Du, S., Kimball, E. A., & Ragains, J. R. (2017). Visible-Light-Promoted Remote C-H Functionalization of o-Diazoniaphenyl Alkyl Sulfones. Organic letters, 19 (20), 5553-5556. https://doi.org/10.1021/acs.orglett.7b02650
