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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

Ajijur Rahaman, Rupali Dasharath Shinde and Sukalyan Bhadra*

*Inorganic Materials and Catalysis Division, CSIR-Central Salt and Marine Chemicals Research Institute, G.B. Marg, Bhavnagar 364002, Gujarat, India, Email: sbhadracsmcri.res.in

A. Rahaman, R. D. Shinde, S. Bhadra, J. Org. Chem., 2023, 88, 1884-1889.

DOI: 10.1021/acs.joc.2c02584


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Abstract

A copper-based system enables methylene insertion between an amine and an alkyne counterpart, via C-N bond cleavage of N,N-dimethylacetamide. The method gives an expedient access to a broad range of propargylic amines in good yields.


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proposed mechanism



Key Words

alkynylation, amination, multicomponent reactions, TBHP


ID: J42-Y2023