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

ABSTRACT: The first-time use of the oxazaborolidine complex in transfer hydrogenation was accomplished. It was prepared without difficulty from cheap materials: ethanolamine and BH₃·THF. A general and efficient method for copper-catalyzed transfer hydrogenation of a variety of N-heteroaromatics with an oxazaborolidine-BH₃ 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.

SUBMITTER: Zhong Y

PROVIDER: S-EPMC6648510 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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

Zhong Yuanhai Y Zhou Taigang T Zhang Zhuohua Z Chang Ruiqing R

ACS omega 20190514 5

The first-time use of the oxazaborolidine complex in transfer hydrogenation was accomplished. It was prepared without difficulty from cheap materials: ethanolamine and BH<sub>3</sub>·THF. A general and efficient method for copper-catalyzed transfer hydrogenation of a variety of N-heteroaromatics with an oxazaborolidine-BH<sub>3</sub> complex under mild reaction conditions afforded the corresponding hydrogenated products in up to 96% yield. Mechanistic studies indicate that the hydrogen source or ...[more]

PMID: 31459938

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