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Alkene 1,2-Difunctionalization by Radical Alkenyl Migration.

ABSTRACT: Transition-metal-free radical ?-perfluoroalkylation with the accompanying vicinal ?-alkenylation of unactivated alkenes is presented. These radical cascades proceed by means of 1,4- or 1,5-alkenyl migration by electron catalysis on readily accessed allylic alcohols. The reactions comprise a regioselective perfluoroalkyl radical addition with subsequent alkenyl migration and concomitant deprotonation to generate a ketyl radical anion that sustains the chain as a single-electron-transfer reducing reagent.

SUBMITTER: Tang X

PROVIDER: S-EPMC5838557 | biostudies-other | 2018 Jan

REPOSITORIES: biostudies-other

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Alkene 1,2-Difunctionalization by Radical Alkenyl Migration.

Tang Xinjun X Studer Armido A

Angewandte Chemie (International ed. in English) 20171214 3

Transition-metal-free radical α-perfluoroalkylation with the accompanying vicinal β-alkenylation of unactivated alkenes is presented. These radical cascades proceed by means of 1,4- or 1,5-alkenyl migration by electron catalysis on readily accessed allylic alcohols. The reactions comprise a regioselective perfluoroalkyl radical addition with subsequent alkenyl migration and concomitant deprotonation to generate a ketyl radical anion that sustains the chain as a single-electron-transfer reducing ...[more]

PMID: 29165859

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