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Aerobic Copper-Promoted Radical-Type Cleavage of Coordinated Cyanide Anion: Nitrogen Transfer to Aldehydes To Form Nitriles

Qian Wu, Yi Luo, Aiwen Lei* and Jingsong You*

*College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. China, Email: jsyouscu.edu.cn, aiwenleiwhu.edu.cn

Q. Wu, Y. Luo, A. Lei, J. You, J. Am. Chem. Soc., 2016, 138, 2885-2888.

DOI: 10.1021/jacs.5b10945 (free Supporting Information)



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Abstract

A copper-promoted C≡N triple bond cleavage of coordinated cyanide anion under a dioxygen atmosphere enables a nitrogen transfer to various aldehydes via a single electron-transfer process. This protocol provides a new cleavage pattern for the cyanide ion and maybe a more useful synthetic pathway to nitriles from aldehydes.

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Key Words

nitriles, oxygen


ID: J48-Y2016