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Fe(III)/NaBH4-Mediated Free Radical Hydrofluorination of Unactivated Alkenes

Timothy J. Barker and Dale L. Boger*

*Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States, Email: bogerscripps.edu

T. J. Barker, D. L. Borger, J. Am. Chem. Soc., 2012, 134, 13588-13591.

DOI: 10.1021/ja3063716 (free Supporting Information)


Abstract

A powerful free radical Markovnikov hydrofluorination of unactivated alkenes is mediated by Fe(III)/NaBH4 using Selectfluor reagent as a source of fluorine. In contrast to the traditional radical hydrofluorination of alkenes, the Fe(III)/NaBH4-mediated reaction is conducted under exceptionally mild reaction conditions, tolerates various functional groups, and even runs open to the air and with water as a cosolvent.

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Key Words

fluorination, Selectfluor


ID: J48-Y2012-2640