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Synthesis of β‐Keto Sulfones via Coupling of Aryl/Alkyl Halides, Sulfur Dioxide and Silyl Enolates through Metal‐Free Photoinduced C–X Bond Dissociation
Author(s) -
Gong Xinxing,
Ding Yechun,
Fan Xiaona,
Wu Jie
Publication year - 2017
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.201700525
Subject(s) - chemistry , alkyl , aryl , photochemistry , silylation , halide , dabco , dissociation (chemistry) , octane , sulfur dioxide , medicinal chemistry , organic chemistry , catalysis
A photoinduced sulfonylative coupling of aryl/alkyl halides, DABCO⋅(SO 2 ) 2 (1,4‐diazabicyclo[2.2.2]octane‐sulfur dioxide), and silyl enolates under metal‐free conditions has been developed, giving rise to β‐keto sulfones in good yields. This transformation proceeds smoothly at room temperature under ultraviolet irradiation with good tolerance of various functional groups. Aryl iodides/bromides and alkyl halides are all good substrates in the sulfonylative reaction. A plausible mechanism is proposed, which proceeds through a radical process under photoinduced conditions.