Copper-Catalyzed Regioselective Cyanation/Diarylmethylation of Formamides: Construction of α-Cyano Functionalized Tetra-Substituted Olefins

Minjing Yuan; Zikang Li; Weifeng Xu; Biquan Xiong; Yu Liu; Min Liu; Ke-Wen Tang; Longzhi Zhu

doi:10.1002/cjoc.202400911

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (2) : 191 -198. DOI: 10.1002/cjoc.202400911

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Copper-Catalyzed Regioselective Cyanation/Diarylmethylation of Formamides: Construction of α-Cyano Functionalized Tetra-Substituted Olefins

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Abstract

Comprehensive Summary:A copper-catalyzed cyanation/diarylmethylation of formamides has been developed for the synthesis of α-cyano functionalized tetra-substituted olefins by utilizing para-quinone methides ( p-QMs) and trimethylcyanosilane as functionalization sources. Various kinds of p-QMs and formamides are well tolerated, delivering the desired products with 72%—94% yields, demonstrating broad functional group tolerance. Notably, the reaction does not require noble metals and proceeds regioselectively under mild conditions. Based on step-by-step control experiments, Hammett studies and DFT calculation, a plausible mechanism is proposed.

Keywords

para-Quinone methides / Cyanation/diarylmethylation / Tetra-substituted olefins / Multicomponent reactions / C—C coupling / C—H activation

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Minjing Yuan, Zikang Li, Weifeng Xu, Biquan Xiong, Yu Liu, Min Liu, Ke-Wen Tang, Longzhi Zhu. Copper-Catalyzed Regioselective Cyanation/Diarylmethylation of Formamides: Construction of α-Cyano Functionalized Tetra-Substituted Olefins. Chinese Journal of Chemistry, 2025, 43(2): 191-198 DOI:10.1002/cjoc.202400911