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Updated: Jan 31, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Direct C-H Carbamoylation of Nitrogen-Containing Heterocycles
Matthieu Jouffroy1, Jongrock Kong1
1Process Research & Development, Merck & Co., Inc., 126 E. Lincoln Ave., Rahway, NJ, 07065, USA.
Abstract:
Nucleophilic radical additions at innately electrophilic C(sp2 ) centers are perfectly suited for the direct functionalization of heterocycles. Using bench stable and commercially available alkyl oxamate and oxamic acid derivatives in combination with photoredox catalysis, a direct carbamoylation of heterocycles yielding amide functionalized pharmacophores in a single step is reported. The reaction conditions reported are compatible with structurally complex heterocyclic substrates of pharmaceutical interest. Notably, derivatives containing functional groups incompatible with standard amidation reactions, such as carboxylic acids and unprotected amines, were found to be amenable to this reaction paradigm.
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