Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 12, Issue 4, Pages 465-469Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201601617
Keywords
catalyst-free; keto sulfones; radical reactions; silylenol ether; sulfur
Categories
Funding
- National Natural Science Foundation of China [21372046, 21532001, 21672037]
- Opening Project of Gannan Medical University Collaborative Innovation Center for Gannan Oil-tea Camellia Industrial Development [YP201607]
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A green approach for the generation of beta-keto sulfones through a reaction of aryldiazonium tetrafluoroborates and sulfur dioxide with silyl enol ether under catalyst-and additive-free conditions has been realized. This reaction proceeds efficiently at room temperature and goes to completion in half an hour. During the reaction process, aryldiazoni-um tetrafluoroborate is treated with DABCO center dot(SO2)(2) (DABCO= 1,4-diazabicyclo[2.2.2]octane) to provide a sulfonyl radical as the key intermediate, which then initiates the transformation. Oxidants or metal catalysts are avoided, and the presence of DABCO also plays an important role in the reaction.
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