Copper-Catalyzed Transfer Hydrogenation of N-Heteroaromatics with an Oxazaborolidine Complex.

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ID: 28199
2019
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Abstract
The first-time use of the oxazaborolidine complex in transfer hydrogenation was accomplished. It was prepared without difficulty from cheap materials: ethanolamine and BH·THF. A general and efficient method for copper-catalyzed transfer hydrogenation of a variety of N-heteroaromatics with an oxazaborolidine-BH complex under mild reaction conditions afforded the corresponding hydrogenated products in up to 96% yield. Mechanistic studies indicate that the hydrogen source originated from water and borane that coordinate with the nitrogen atom of oxazaborolidine. Accordingly, a plausible mechanism for this reaction was proposed. This method was successfully used in the key step synthesis of natural products (±)-angustureine and (±)-galipinine in three steps.
Reference Key
zhong2019coppercatalyzedacs Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Zhong, Yuanhai;Zhou, Taigang;Zhang, Zhuohua;Chang, Ruiqing;
Journal ACS omega
Year 2019
DOI
10.1021/acsomega.9b00930
URL
Keywords Keywords not found

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