Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202217638
Keywords
Benzylamides; Benzylamines; Copper; Enantioselectivity; Photocatalysis
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A method for direct access to enantioenriched benzylic amides and carbamate-protected primary benzylamines by C-H functionalization is reported. The enantioselective intermolecular dehydrogenative C-N bond formation is enabled by a combination of a chiral copper catalyst, a photocatalyst, and an oxidant, and it takes place under mild conditions, which allow for a broad substrate scope. The method is compatible with late-stage C-H functionalization and provides easy access to N-15-labeled amides and amines starting from cheap (NH4Cl)-N-15.
A method for direct access to enantioenriched benzylic amides and carbamate-protected primary benzylamines by C-H functionalization is reported. The C-H substrate is used as limiting reagent with only a small excess of the unactivated amide or carbamate nucleophile. The enantioselective intermolecular dehydrogenative C-N bond formation is enabled by a combination of a chiral copper catalyst, a photocatalyst, and an oxidant, and it takes place under mild conditions, which allow for a broad substrate scope. The method is compatible with late-stage C-H functionalization, and it provides easy access to N-15-labeled amides and amines starting from cheap (NH4Cl)-N-15.
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