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Renewable Molecular Flasks with NADH Models: Combination of Light‐Driven Proton Reduction and Biomimetic Hydrogenation of Benzoxazinones
Author(s) -
Zhao Liang,
Wei Jianwei,
Lu Junhua,
He Cheng,
Duan Chunying
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201702926
Subject(s) - chemistry , nicotinamide adenine dinucleotide , redox , active site , combinatorial chemistry , catalysis , photochemistry , nanotechnology , nad+ kinase , enzyme , organic chemistry , materials science
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.