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August 22, 2025The Journal of Organic Chemistry

Aryl Radical-Initiated Synthesis of Unsymmetrically Bicyclo[1.1.1]pentane Sulfides

Yanchuang Zhao Qiujin Fan Y. Xie Wenhai Huang Yun Zhe Ji Xinxin Shao

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Key Points

This method offers a practical way to synthesize various BCP-sulfides using mild conditions.
A notable feature of the process is the creation of both aryl and alkyl radicals through an XAT mechanism.
Utilizing bench-stable zinc thiolates allows for efficient coupling in radical synthesis.
Mechanistic insights reveal the dual role of zinc thiolates as both radical initiators and coupling agents.

Implication

This work demonstrates a new multicomponent reaction using zinc thiolates and aryldiazonium salt, suggesting efficient synthesis of BCP-sulfides.

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Cite This Study

Zhao et al. (2025) studied this question.

synapsesocial.com/papers/68c1ce7054b1d3bfb60f5bbc https://doi.org/10.1021/acs.joc.5c01660

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