Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 9, Pages 2217-2221Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201806159
Keywords
alkyl oxamate; carbamoylation; C-H functionalization; heterocycles; photoredox catalysis
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Nucleophilic radical additions at innately electrophilic C(sp(2)) 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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