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Published on: August 12, 2019
Metal free biomimetic deaminative direct C-C coupling of unprotected primary amines with active methylene compounds
Santanu Ghosh1, Chandan K Jana1
1Department of Chemistry, Indian Institute of Technology Guwahati, 780139, India. ckjana@iitg.ac.in.
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.
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