Photo-induced reductive cross-coupling of aldehydes, ketones and imines with electron-deficient arenes to construct aryl substituted alcohols and amines

doi:10.1016/S1872-2067(17)62896-1

Chinese Journal of Catalysis ›› 2018, Vol. 39 ›› Issue (3): 487-494.DOI: 10.1016/S1872-2067(17)62896-1

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Photo-induced reductive cross-coupling of aldehydes, ketones and imines with electron-deficient arenes to construct aryl substituted alcohols and amines

Zan Liu^a,b, Xiaolei Nan^a,b, Tao Lei^a,b, Chao Zhou^a,b, Yang Wang^a,b, Wenqiang Liu^a,b, Bin Chen^a,b, Chenho Tung^a,b, Lizhu Wu^a,b

a Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received:2017-09-17 Revised:2017-10-26 Online:2018-03-18 Published:2018-03-10
Contact: 10.1016/S1872-2067(17)62896-1
Supported by:
This work was supported by the Ministry of Science and Technology of China (2013CB834804, 2014CB239402), the National Natural Science Foundation of China (21390404, 91427303), and the Strategic Priority Research Program of the Chinese Academy of Science (XDB17030400).

Abstract

Abstract:

Umpolung reactions of C=X bonds (X=O, N) are valuable ways of constructing new C-C bonds, which are sometimes difficult to be constructed using traditional synthetic pathways. Classical polarity inversion of C=X bonds (X=O, N) usually requires air or moisture-sensitive and strong reducing agents, which limit the feasibility of substrate scope. Herein we describe a photo-induced reductive cross-coupling reaction of aldehydes, ketones and imines with electron-deficient arenes (aromatic nitriles) using fac-Ir(ppy)₃ as a photocatalyst and diisopropylethylamine (DIPEA) as a terminal reductant under visible light irradiation. Mild conditions and high yields mean that this new polarity inversion strategy can be used with aryl-substituted alcohols and amines. Spectroscopic studies and control experiments have demonstrated the oxidative quenching of Ir(ppy)₃^* by electron-deficient arenes involved in the key step for the C-C bond formation.

Key words: Aryl substituted alcohols and amines, Radical-radical cross coupling, Polarity reversal, Photocatalysis, Arylation

Zan Liu, Xiaolei Nan, Tao Lei, Chao Zhou, Yang Wang, Wenqiang Liu, Bin Chen, Chenho Tung, Lizhu Wu. Photo-induced reductive cross-coupling of aldehydes, ketones and imines with electron-deficient arenes to construct aryl substituted alcohols and amines[J]. Chinese Journal of Catalysis, 2018, 39(3): 487-494.

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Photo-induced reductive cross-coupling of aldehydes, ketones and imines with electron-deficient arenes to construct aryl substituted alcohols and amines

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