Open-Shell Fluorination of Alkyl Bromides: Unexpected Selectivity in a Silyl Radical-Mediated Chain Process

Gabrielle H. Lovett, Shuming Chen, Xiao-Song Xue, K. N. Houk* and David W. C. MacMillan*

*University of California, Los Angeles, California 90095; Princeton University, Princeton, New Jersey 08544, United States, Email: houkchem.ucla.edu, dmacmillprinceton.edu

G. H. Lovett, S. Chen, X.-S. Xue, K. N. Houk, D. W. C. MacMillan, J. Am. Chem. Soc., 2019, 141, 20031-20036.

DOI: 10.1021/jacs.9b11434

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Abstract

The combination of silyl radical-mediated halogen-atom abstraction and benzophenone photosensitization enables a fluorination of alkyl bromides. Selectivity for halogen-atom abstraction over Si-F bond formation is observed in the presence of an electrophilic fluorinating reagent containing a weak N-F bond.

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Key Words

fluorination, NFSI, photochemistry

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ID: J48-Y2019