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论文类型：期刊论文

发表时间：2017-07-17

发表刊物：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录刊物：SCIE、EI、PubMed

卷号：56

期号：30

页面范围：8692-8696

ISSN号：1433-7851

关键字：biomimetic hydrogenation; molecular flasks; proton reduction; renewable active sites; supramolecular chemistry

摘要：Using small molecules with defined pockets to catalyze chemical transformations resulted in attractive catalytic syntheses that echo the remarkable properties of enzymes. By modulating the active site of a nicotinamide adenine dinucleotide (NADH) model in a redox-active molecular flask, we combined biomimetic hydrogenation with in situ regeneration of the active site in a one-pot transformation using light as a clean energy source. This molecular flask facilitates the encapsulation of benzoxazinones for biomimetic hydrogenation of the substrates within the inner space of the flask using the active sites of the NADH models. The redox-active metal centers provide an active hydrogen source by light-driven proton reduction outside the pocket, allowing the in situ regeneration of the NADH models under irradiation. This new synthetic platform, which offers control over the location of the redox events, provides a regenerating system that exhibits high selectivity and efficiency and is extendable to benzoxazinone and quinoxalinone systems.