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Light-Switchable N-Alkylation Using Amine-Functionalized MOF
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AI
DOI：10.1016/j.apcatb.2024.123924.png)
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Abstract
En 中文
Catalytic N -alkylation is a frequently employed method to synthesize secondary amines and imines, yet selectivity control remains as a challenge that normally requires specialized catalysts under harsh reaction conditions. Here we propose a light-switchable N -alkylation of amines with aromatic halides for selective synthesis of secondary amines and imines, using an amine-functionalized metal-organic framework (MIL-125-NH 2 ) under mild conditions. The MIL-125-NH 2 catalyst possesses Lewis acidic sites, which catalyze direct dehalogenative condensation of bromides with primary amines to produce secondary amines in the dark. Upon irradiation, the MIL-125-NH 2 reduces molecular oxygen to create oxygen radicals, converting bromides into the corresponding aldehydes to yield imines via a dehydrative coupling with amines. With appropriate acidity, rapid oxygen reduction kinetics, and optimized adsorption of aromatic bromides and generated water, the system catalyzes the conversion of a wide range of substrates, thus featuring it a promising method for applications.
Keywords:
Heterogeneous catalysis
Photocatalysis
N -alkylation
Selective C -N cross coupling
Metal organic frameworks
Journal
A
IF:
21.1
Papers:
4.2K
Citations:
18.2W
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