Copper-Catalyzed Regioselective Iodoformylation of Terminal Alkynes to Access Versatile Electrophiles (E)-β-Iodo-α,β-Unsaturated Aldehydes

Dong Lu, Xiaogang Yang, Wenjian Guan, Shuang-Feng Yin, Nobuaki Kambe and Renhua Qiu*

*State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China, Email: renhuaqiu1hnu.edu.cn

D. Lu, X. Yang, W. Guan, S.-F. Yin, N. Kambe, R. Qiu, Org. Lett., 2022, 24, 6993-6998.

DOI: 10.1021/acs.orglett.2c02838

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Abstract

A CuI-catalyzed iodoformylation of terminal alkynes with TMSCF₃ and NaI provides (E)-β-iodo-α,β-unsaturated aldehydes with excellent chemoselectivity, regioselectivity, and stereoselectivity. This synthetic method uses inexpensive and easy-to-handle chemical feedstocks. Synthetic applications of the (E)-β-iodo-α,β-unsaturated aldehydes are demonstrated.

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Key Words

formylation, iodination

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ID: J54-Y2022