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Updated: Jul 15, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Catalysis of stannane-mediated radical chain reactions by benzeneselenol
David Crich1, Daniel Grant, Venkataramanan Krishnamurthy
1Department of Chemistry, University of Illinois at Chicago, IL 60607-7061, USA. dcrich@uic.edu
Abstract:
The discovery and development of the catalysis of stannane-mediated radical chain reactions by benzeneselenol, generated in situ by reduction of diphenyl diselenide with tributyltin hydride, are described. The catalytic sequence is discussed in terms of polarity reversal catalysis of radical chain reactions, and applications to synthesis are presented. These include the prevention of numerous radical rearrangement reactions, the ability to intervene in certain multistep radical rearrangements, especially aryl and vinyl radical cyclizations, at intermediate stages with advantages to the product profile, and the effective trapping of allyl-, benzyl-, and cyclohexadienyl-type radicals, permitting inter alia the isolation of aryl cyclohexadienes and their application in synthesis.
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