SynOpen (Jan 2021)

Simple and Efficient Synthesis of Allyl Sulfones through Cs2CO3-Mediated Radical Sulfonylation of Morita–Baylis–Hillman Adducts with Thiosulfonates

  • Angothu Shankar,
  • Md. Waheed,
  • Raju Jannapu Reddy

DOI
https://doi.org/10.1055/a-1422-9411
Journal volume & issue
Vol. 05, no. 01
pp. 91 – 99

Abstract

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A highly efficient and eco-friendly method has been developed for the synthesis of allyl sulfones using Morita–Baylis–Hillman (MBH) adducts and thiosulfonates under mild conditions. The Cs2CO3-promoted radical sulfonylation provided a series of allyl sulfones in good to high yields with high stereoselectivities. A wide variety of MBH bromides/acetates as well as thiosulfonates were tolerated and reliable in scaled-up synthesis. A plausible mechanism is proposed to rationalize the radical sulfonylation.

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