Sequential Ring Opening/In Situ SO2-Capture/Alkynylation of Cyclopropanols with Alkynyl Triflones Initiated by Energy Transfer

Guohua Fan; Changfu Wu; Xiaozu Liu; Peijun Liu

doi:10.1021/acs.joc.4c00341

Sequential Ring Opening/In Situ SO₂-Capture/Alkynylation of Cyclopropanols with Alkynyl Triflones Initiated by Energy Transfer

J Org Chem. 2024 May 15. doi: 10.1021/acs.joc.4c00341. Online ahead of print.

Authors

Guohua Fan¹, Changfu Wu¹, Xiaozu Liu^{1

2}, Peijun Liu^{1

2}

Affiliations

¹ Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563000, China.
² Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi 563000, China.

PMID: 38745550
DOI: 10.1021/acs.joc.4c00341

Abstract

A visible-light-triggered ring opening/in situ SO₂-capture/alkynylation sequence of cyclopropyl alcohols with alkynyl triflones using 4CzIPN as a triplet energy transfer photocatalyst is herein described. This metal-free protocol provides a straightforward and atom-economical approach to alkynyl-substituted γ-keto sulfones with a broad scope of substituents. In this transformation, alkynyl triflones could be used as both radical acceptors and SO₂ donors. Preliminary experimental mechanistic studies and synthetic utility are also demonstrated.