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Catalytic Methylene Insertion between Amines and Terminal Alkynes via C-N Bond Cleavage of N,N-Dimethylacetamide: A Unique Route to Propargylic Amines

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JOURNAL OF ORGANIC CHEMISTRY
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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02584

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A copper-based system enables the methylene insertion reaction between an amine and a milder nucleophile, such as a terminal alkyne, through the cleavage of the C-N bond in N,N-dimethylacetamide. This method provides a convenient access to propargylic amines with good to excellent yields. The wide substrate scope and the ability to functionalize complex molecules at late stages make this protocol practically valuable.
A copper-based system allows for the methylene insertion between an amine and a milder nucleophile, including a terminal alkyne counterpart, via C-N bond cleavage of N,Ndimethylacetamide. The method gives an expedient access to propargylic amines in good to excellent yields. A wide-ranging substrate scope and late-stage functionalization of complex molecules make the protocol practically valuable.

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