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Sodium Dithionite‐Mediated Decarboxylative Sulfonylation: Facile Access to Tertiary Sulfones
Author(s) -
Li Yaping,
Chen Shihao,
Wang Ming,
Jiang Xuefeng
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202001589
Subject(s) - decarboxylation , sodium dithionite , chemistry , electrophile , steric effects , heteroatom , dithionite , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , ring (chemistry) , enzyme
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.