American Chemical Society
ol2c02838_si_001.pdf (20.18 MB)

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

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journal contribution
posted on 2022-09-19, 19:07 authored by Dong Lu, Xiaogang Yang, Wenjian Guan, Shuang-Feng Yin, Nobuaki Kambe, Renhua Qiu
Herein, we describe a method for synthesizing (E)-β-iodo-α,β-unsaturated aldehydes via the iodoformylation of terminal alkynes with TMSCF3 and NaI. This synthetic method uses inexpensive and easy-to-handle chemical feedstocks and employs a commercially available CuI catalyst. It can transform a broad range of terminal alkynes into bis-electrophile (E)-β-iodo-α,β-unsaturated aldehydes with excellent chemoselectivity, regioselectivity, and stereoselectivity. Moreover, it was demonstrated that this protocol has abundant organic reactivity.