Energy Transfer (EnT)-Mediated Stereoselective Aryl-Heterofunctionalization of Unactivated Alkynes via Radical Rearrangement

Xin Chao Meng, Tian Xiong Pan, Feng Yang, Hai Xi Zhu, Yu Wen Huang, Bo Rong Leng, De Cai Wang, Yi Long Zhu

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

In this study, we present a novel catalyst-free energy transfer mediated radical rearrangement strategy for the aryl-heterofunctionalization of unactivated alkynes, leading to the synthesis of polyfunctional olefins with exceptional stereoselectivity. This innovative approach, driven by visible light, exemplifies green chemistry principles by eliminating the reliance on transition metals, external oxidants, and photocatalysts. The broad applicability of our method is demonstrated through the successful synthesis of a diverse array of compounds, including vinyl sulfones, vinyl selenides, and vinyl sulfides. Preliminary mechanistic insights suggest an energy transfer mechanism, highlighting the efficiency and selectivity of this novel strategy.

Original languageEnglish
Pages (from-to)1061-1070
Number of pages10
JournalJournal of Organic Chemistry
Volume90
Issue number2
DOIs
StatePublished - 17 Jan 2025

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