CuI/N4 ligand/TEMPO derivatives: A mild and highly efficient system for aerobic oxidation of primary alcohols

doi:10.1016/S1872-2067(14)60161-3

Abstract

Abstract:

A new system consisting of a copper(I) complex generated in situ from a tetradentate nitrogen ligand and CuI in combination with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) derivatives was successfully developed. The system was suitable for efficient and selective aerobic oxidation of primary benzyl and allyl alcohols with a wide range of functional groups to the corresponding aldehydes at room temperature. The best result was obtained with N,N'-dimethyl-N,N'-bis(2- pyridylmethyl)ethane-1,2-diamine as the ligand and 4-OH-TEMPO as a cocatalyst in CH₃CN. In addition, high-resolution mass spectrometry, ultraviolet-visible spectroscopy, and electrochemical experiments were used to provide evidence of intermediates.

Key words: Alcohol, Aerobic oxidation, Tetradentate nitrogen ligand, Copper, 2,2,6,6-tetramethylpiperidine-1-oxyl

Shufang Zhang, Chengxia Miao, Daqian Xu, Wei Sun, Chungu Xia. CuI/N4 ligand/TEMPO derivatives: A mild and highly efficient system for aerobic oxidation of primary alcohols[J]. Chinese Journal of Catalysis, 2014, 35(11): 1864-1873.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60161-3

https://www.cjcatal.com/EN/Y2014/V35/I11/1864

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