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Updated: Sep 19, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Selective Functionalization of Benzene Ring via Carbene-Initiated [4,5]-Rearrangement
Jiarong Shi1, Xuerong Wang1, Chuang Mei1
1School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 401331, P. R. China.
Abstract:
The extreme similarity in electronic and steric reactivity among the C─H bonds present on alkyl-substituted aromatic rings presents a formidable challenge when it comes to achieving high selectivity during the para-selective functionalization of these bonds. This article presents a unique study that delves into the para-selective functionalization or dearomatization functionalization of benzene rings, achieved through the reaction of carbenes with allyl sulfoxides. Mechanistic investigations suggest that the transformation likely proceeds via an uncommon carbene-mediated [4,5]-rearrangement process.
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