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A General Approach to Site-Specific, Intramolecular C-H Functionalization Using Dithiocarbamates.

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.

SUBMITTER: Na CG

PROVIDER: S-EPMC6249686 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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A General Approach to Site-Specific, Intramolecular C-H Functionalization Using Dithiocarbamates.

Na Christina G CG Alexanian Erik J EJ

Angewandte Chemie (International ed. in English) 20180903 40

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 t ...[more]

PMID: 30085389

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