Sodium Dithionite-Mediated Decarboxylative Sulfonylation: Facile Access to Tertiary Sulfones

Angewandte Chemie
Yaping LiXuefeng Jiang

Abstract

A straightforward multicomponent decarboxylative cross coupling of redox-active esters (N-hydroxyphthalimide ester), sodium dithionite, and electrophiles was established to construct sterically bulky sulfones. The inorganic salt sodium dithionite not only served as the sulfur dioxide source, but also acted as an efficient radical initiator for the decarboxylation. Notably, diverse naturally abundant carboxylic acids and artificially prepared carboxyl-containing drugs with multiple heteroatoms and sensitive functional groups successfully underwent this decarboxylative sulfonylation to provide sterically bulky tertiary sulfones. Mechanistic studies further demonstrated that decarboxylation was the rate-determining step and occurred via a single-electron transfer (SET) process with the assistance of sodium dithionite.

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Citations

Jan 5, 2021·Chemical Communications : Chem Comm·Tonghao ZhuJie Wu
Jun 24, 2021·Journal of the American Chemical Society·Patrick J SarverDavid W C MacMillan
Sep 4, 2021·Nature Communications·Zikun WangXihe Bi
Oct 9, 2021·The Journal of Organic Chemistry·Fengjuan ChenWei Zeng
Oct 22, 2021·The Journal of Organic Chemistry·Qiaomei JinJian Zhang

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