4.7 Article

Synthesis of α-Aminoacetals via Decarboxylative Coupling of Imine and 2,2,-Diethoxyacetic Acid

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JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 10, 页码 6532-6537

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01941

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In this study, the photocatalytic synthesis of alpha-aminoacetals via decarboxylative coupling of imine and 2,2-diethoxyacetic acid was achieved using a nonstoichiometric amount of a radical initiator. Various functional groups were compatible, providing efficient one-step access to diversely functionalized alpha-aminoacetals, which shows great potential for further research.
Atom-economical C-C coupling between imines and a C1 source could provide alpha-aminoaldehyde derivatives. Nevertheless, such a coupling has rarely been achieved owing to the lack of appropriate nucleophilic C1 sources. In this study, photocatalytic synthesis of alpha-aminoacetals was achieved via decarboxylative coupling of imine and 2,2-diethoxyacetic acid using a nonstoichiometric amount of a radical initiator. Various functional groups were compatible, providing efficient one-step access to diversely functionalized alpha-aminoacetals, which provides a promising platform for further research.

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