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Updated: Sep 10, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Aryl Radical-Initiated Synthesis of Unsymmetrically Bicyclo[1.1.1]pentane Sulfides
Yanchuang Zhao1, Qiujin Fan1, Yule Xie1
1Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Zhejiang Key Laboratory of Organosilicon Material Technology, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang 311121, PR China.
Abstract:
Here, we developed an efficient halogen atom transfer (XAT)-enabled multicomponent reaction (MCR) between [1.1.1]propellane, zinc thiolates, and alkyl iodides utilizing aryldiazonium salt as the promoter. Moreover, direct aryl-thiolation of [1.1.1]propellane in the absence of alkyl iodides was also described. Thus, these chemoselective reactions provide a practical approach to construct a variety of aryl- or alkyl-substituted BCP-sulfides under mild reaction conditions. Mechanistic studies support that the aryl radical generated by the interaction between aryldiazonium salt and zinc thiolate undergoes a rapid XAT process to deliver the corresponding alkyl radical. Notably, the bench-stable zinc thiolates play dual roles, including the initiator of aryl radical and coupling partner.
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