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Issue 48, 2019
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Metal free biomimetic deaminative direct C–C coupling of unprotected primary amines with active methylene compounds

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Abstract

An unprecedented direct C–C coupling reaction of unprotected primary amines with active methylene compounds is reported. The reaction involves a biomimetic deamination of amines which was achieved under conditions free of metallic reagents and strong oxidizing agents. A wide range of primary amines was reacted with different active methylene compounds to provide structurally diverse trisubstituted alkenes and dihydropyridines. A kinetic study revealed an activation barrier of 10.1 kcal mol−1 for the conversion of a key intermediate of the reaction.

Graphical abstract: Metal free biomimetic deaminative direct C–C coupling of unprotected primary amines with active methylene compounds

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Publication details

The article was received on 07 Oct 2019, accepted on 19 Nov 2019 and first published on 19 Nov 2019


Article type: Communication
DOI: 10.1039/C9OB02163A
Org. Biomol. Chem., 2019,17, 10153-10157

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    Metal free biomimetic deaminative direct C–C coupling of unprotected primary amines with active methylene compounds

    S. Ghosh and C. K. Jana, Org. Biomol. Chem., 2019, 17, 10153
    DOI: 10.1039/C9OB02163A

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