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Selective [3 + 2] Cycloaddition of Cyclopropenone Derivatives and Elemental Chalcogens

Jian Wu, Wen-Xia Gao, Xiao-Bo Huang, Yun-Bing Zhou*, Miao-Chang Liu* and Hua-Yue Wu

*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 325035, P. R. of China, Email: zybwzu.edu.cn, mclwzu.edu.cn

J. Wu, W.-X. Gao, X.-B. Huang, Y.-B. Zhou, M.-C. Liu, H.-Y. Wu, Org. Lett., 2020, 22, 5555-5560.

DOI: 10.1021/acs.orglett.0c01914 (free Supporting Information)



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Abstract

A highly efficient [3 + 2] cycloaddition of cyclopropenone derivatives and elemental chalcogens provides 1,2-dichalcogen heterocycles under mild reaction conditions. Different from other cyclopropenone derivatives, cyclopropenselenones undergo unprecedented rearrangement with elemental sulfur. This protocol offers excellent atom economy, gram-scale ability, and good regioselectivity.

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Key Words

S-heterocycles


ID: J54-Y2020