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Synthesis of γ‐Keto Sulfones through a Three‐Component Reaction of Cyclopropanols, DABCO ⋅ (SO 2 ) 2 and Alkyl Halides
Author(s) -
Zhang Chun,
Zhang Chao,
Tang Jie,
Ye Shengqing,
Ma Mingliang,
Wu Jie
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100066
Subject(s) - chemistry , alkyl , halide , dabco , nitro , nucleophile , nucleophilic substitution , medicinal chemistry , catalysis , organic chemistry
A route to γ‐keto sulfones through a metal‐free reaction of cyclopropanols, DABCO ⋅ (SO2)2 and alkyl halides is described. This reaction occurs under mild conditions in the absence of any catalysts, additives, or oxidants. Various functional groups including as ester, amino, methoxy, bromo, trifluoromethyl, nitro and carbonyl are tolerated well in this transformation, and the corresponding γ‐keto sulfones are afforded in 35% to 95% yields. The proposed mechanism implies that this reaction proceeds through γ‐keto sulfinate intermediate generated in situ, which further undergoes nucleophilic substitution with alkyl halides leading to γ‐keto sulfones.