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:10.1055/a-1422-9411

SynOpen, Inhaltsverzeichnis

CC BY-NC-ND 4.0 · SynOpen 2021; 05(01): 91-99
DOI: 10.1055/a-1422-9411

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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 ∗

Abstract

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Abstract

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.

Key words

allyl sulfones - cesium carbonate - MBH adducts - radical sulfonylation - thiosulfonates

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Referenzen

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