Photocatalyst-free chemoselective radical-relay strategy enabled cyanoalkyl difunctionalization of alkenes via catalytic EDA complex

doi:10.1016/S1872-2067(26)64995-9

Abstract

Abstract: The electron donor-acceptor (EDA) strategy has emerged as a sustainable alternative in photochemistry, enabling the generation of radicals without any photocatalysts. However, the formation of the EDA complex often requires stoichiometric donors, resulting in excessive waste of the electron donors, and the catalytic EDA strategy remains challenging. Herein, a novel catalytic EDA complex, employing N-(4-bromophenyl)-N-phenylnaphthalen-1-amine as the catalytic electron donor and O-aryl oximes as electron acceptors, was described to achieve cyanoalkyl difunctionalization of alkenes via a radical-relay strategy under visible-light irradiation. Various versatile compounds with cyanoalkyl and 1,4-dicarbonyl groups could be easily synthesized under green and sustainable reaction conditions. The significance of this sustainable methodology was highlighted by the novel catalytic EDA complex, broad substrate scope (36 examples), green solvent, good synthetic applications, and high selectivity.

Key words: Catalytic electron donor-acceptor, Radical relay, Triarylamines, Difunctionalization, Cyanoalkylation

Hao-Cong Li, Ming Zhang, Heng-Bo Yang, Xiao-Lan Chen, Qiyan Lv, Lingbo Qu, Bing Yu. Photocatalyst-free chemoselective radical-relay strategy enabled cyanoalkyl difunctionalization of alkenes via catalytic EDA complex[J]. Chinese Journal of Catalysis, DOI: 10.1016/S1872-2067(26)64995-9.

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