Convenient Ambient Temperature Generation of Sulfonyl Radicals

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doi:10.1071/CH12499

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Affiliated with RACI

Royal Australian
Chemical Institute

Convenient Ambient Temperature Generation of Sulfonyl Radicals

Kerry Gilmore ^A , Brian Gold ^A , Ronald J. Clark ^A and Igor V. Alabugin ^A ^B

^A Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA.
^B Corresponding author. Email: alabugin@chem.fsu.edu

Australian Journal of Chemistry 66(3) 336-340 http://dx.doi.org/10.1071/CH12499
Submitted: 7 November 2012 Accepted: 12 December 2012 Published: 16 January 2013





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Abstract

Presented herein is a novel method for the efficient, ambient temperature generation of sulfonyl radicals from aryl and alkyl sulfonylbromides upon autoxidation of triethylborane (Et₃B). The resultant radicals were regioselectively trapped via addition to terminal alkynes, generating a secondary vinyl radical that selectively abstracts a Br atom from RSO₂Br, yielding the (E)-bromo vinylsulfones. Sensitivity towards Lewis basic groups was observed, presumably due to the disruptive coordination to Et₃B before atom-transfer.

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