Christina G Na1, Erik J Alexanian1. 1. Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599, USA.
Abstract
Intramolecular hydrogen atom transfer is an established approach for the site-specific functionalization of unactivated, aliphatic C-H bonds. Transformations using this strategy typically require unstable intermediates formed using strong oxidants and have mainly targeted C-H halogenations or intramolecular aminations. Herein, we report a site-specific C-H functionalization that significantly increases the synthetic scope and convergency of reactions proceeding via intramolecular hydrogen atom transfer. Stable, isolable N-dithiocarbamates are used as precursors to amidyl radicals formed via either light or radical initiation to efficiently deliver highly versatile alkyl dithiocarbamates across a wide range of complex structures.
Intramolecularn class="Chemical">hydrogen atom transfer is an established approach for the site-specific functionalization of unactivated, aliphatic C-H bonds. Transformations using this strategy typically require unstable intermediates formed using strong oxidants and have mainly targeted C-H halogenations or intramolecular aminations. Herein, we report a site-specific C-H functionalization that significantly increases the synthetic scope and convergency of reactions proceeding via intramolecularhydrogen atom transfer. Stable, isolable N-dithiocarbamatesare used as precursors to amidyl radicals formed via either light or radical initiation to efficiently deliver highly versatile alkyl dithiocarbamates across a wide range of complex structures.
Authors: Andrew D Chen; James H Herbort; Ethan A Wappes; Kohki M Nakafuku; Darsheed N Mustafa; David A Nagib Journal: Chem Sci Date: 2020-01-31 Impact factor: 9.825