title: Synthesis of β-Keto Sulfones by a Catalyst-Free Reaction of Aryldiazonium Tetrafluoroborates, Sulfur Dioxide, and Silyl Enol Ethers.
abstract: 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.
authors.affiliation: Gannan Medical University, Collaborative Innovation Center for Gannan Oil-tea Camellia Industrial Development, 1 Yixueyuan Road, Ganzhou, Jiangxi, 341000, China.|Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.
authors.forename: Tianshuo
authors.initials: T
authors.lastname: Liu
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.
authors.forename: Danqing
authors.initials: D
authors.lastname: Zheng
authors.affiliation: Gannan Medical University, Collaborative Innovation Center for Gannan Oil-tea Camellia Industrial Development, 1 Yixueyuan Road, Ganzhou, Jiangxi, 341000, China.
authors.forename: Yechun
authors.initials: Y
authors.lastname: Ding
authors.affiliation: Gannan Medical University, Collaborative Innovation Center for Gannan Oil-tea Camellia Industrial Development, 1 Yixueyuan Road, Ganzhou, Jiangxi, 341000, China.
authors.forename: Xiaona
authors.initials: X
authors.lastname: Fan
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Wu
keywords: catalyst-free; keto sulfones; radical reactions; silyl enol ether; sulfur