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Updated: May 3, 2026

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Regiodivergent synthesis of 1- and 2-arylsulfonyl 1,3-dienes
Carissa S Hampton1, Michael Harmata
1Department of Chemistry, University of Missouri-Columbia , 601 South College Avenue, Columbia, Missouri 65211, United States.
Abstract:
In the course of a study of the alkoxyallylation of allenic sulfones through the use of π-allylpalladium chemistry, we discovered an isomerization of allenic sulfones to arylsulfonyl 1,3-dienes. Under conditions of palladium catalysis in the presence of acids such as acetic acid, allenic sulfones are converted to 1-arylsulfonyl 1,3-dienes. On the other hand, nucleophilic catalysis using triphenylphosphine in the presence of a proton shuttle yields 2-arylsulfonyl 1,3-dienes. Thus, either regioisomer of the arylsulfonyl diene can be prepared at will based on changes in reaction conditions.
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