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?-Perfluoroalkyl-?-alkynylation of alkenes via radical alkynyl migration.

ABSTRACT: Transition metal-free radical ?-perfluoroalkylation with concomitant ?-alkynylation of unactivated alkenes is presented. These cascades proceed via electron-catalysis and comprise a radical 1,4- or 1,5-alkynyl migration from tertiary propargylic alcoholates to secondary or tertiary C-radicals as the key step. Alkynyl migration leads to a ketyl radical anion that sustains the chain as a single electron transfer reducing reagent.

SUBMITTER: Tang X

PROVIDER: S-EPMC5637125 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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α-Perfluoroalkyl-β-alkynylation of alkenes <i>via</i> radical alkynyl migration.

Tang Xinjun X Studer Armido A

Chemical science 20170804 10

Transition metal-free radical α-perfluoroalkylation with concomitant β-alkynylation of unactivated alkenes is presented. These cascades proceed <i>via</i> electron-catalysis and comprise a radical 1,4- or 1,5-alkynyl migration from tertiary propargylic alcoholates to secondary or tertiary C-radicals as the key step. Alkynyl migration leads to a ketyl radical anion that sustains the chain as a single electron transfer reducing reagent. ...[more]

PMID: 29147514

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