Synthesis of β-Keto Sulfones by a Catalyst-Free Reaction of Aryldiazonium Tetrafluoroborates, Sulfur Dioxide, and Silyl Enol Ethers

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• 作者：Tianshuo Liu ; Danqing Zheng ; Yechun Ding ; Dr. Xiaona Fan and Prof. Dr. Jie Wu
• 刊名：Chemistry – An Asian Journal
• 出版年：2017
• 出版时间：February 16, 2017
• 年：2017
• 卷：12
• 期：4
• 页码：465-469
• 全文大小：755K
• ISSN：1861-471X

文摘

A green approach for the generation of β-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, aryldiazonium tetrafluoroborate is treated with DABCO⋅(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.