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Visible-Light-Induced Formation of Thiavinyl 1,3-Dipoles: A Metal-Free [3+2] Oxidative Cyclization with Alkynes as Easy Access to Thiophenes

Baihui Zheng, Xiaotong Li, Yang Song, Shuyang Meng, Yifei Li, Qun Liu and Ling Pan*

*Jilin Province Key Laboratory of Organic Functional Molecular, Design & Synthesis, Department of Chemistry, Northeast Normal University, 5268 Renmin Street, Changchun 130024, China, Email:

B. Zheng, X. Li, Y. Song, S. Meng, Y. Li, Q. Liu, L. Pan, Org. Lett., 2021, 23, 3453-3459.

DOI: 10.1021/acs.orglett.1c00915

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A visible-light-induced [3+2] oxidative cyclization of various alkynes with easily available ketene dithioacetals as thiavinyl 1,3-dipoles provides multisubstituted thiophenes in good yields under very mild metal-free conditions in the presence of an acridine photosensitizer. This reaction tolerates a wide range of substrates and achieves good efficiency in large-scale syntheses.

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Key Words

thiophenes, photochemistry

ID: J54-Y2021