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Fe(III)/NaBH4-mediated free radical hydrofluorination of unactivated alkenes.

ABSTRACT: A powerful Fe(III)/NaBH(4)-mediated free radical hydrofluorination of unactivated alkenes is disclosed using Selectfluor reagent as a source of fluorine and resulting in exclusive Markovnikov addition. In contrast to the traditional and unmanageable free radical hydrofluorination of alkenes, the Fe(III)/NaBH(4)-mediated reaction is conducted under exceptionally mild reaction conditions (0 °C, 5 min, CH(3)CN/H(2)O). The reaction can be conducted open to the air and with water as a cosolvent and demonstrates an outstanding substrate scope and functional group tolerance.

SUBMITTER: Barker TJ

PROVIDER: S-EPMC3425717 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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Fe(III)/NaBH4-mediated free radical hydrofluorination of unactivated alkenes.

Barker Timothy J TJ Boger Dale L DL

Journal of the American Chemical Society 20120807 33

A powerful Fe(III)/NaBH(4)-mediated free radical hydrofluorination of unactivated alkenes is disclosed using Selectfluor reagent as a source of fluorine and resulting in exclusive Markovnikov addition. In contrast to the traditional and unmanageable free radical hydrofluorination of alkenes, the Fe(III)/NaBH(4)-mediated reaction is conducted under exceptionally mild reaction conditions (0 °C, 5 min, CH(3)CN/H(2)O). The reaction can be conducted open to the air and with water as a cosolvent and d ...[more]

PMID: 22860624

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