ArticleNature communications2023
Site- and enantioselective cross-coupling of saturated N-heterocycles with carboxylic acids by cooperative Ni/photoredox catalysis.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 79 citations in OpenAlex.
- Regio-, Stereo-, and Enantioselective C(spAngewandte Chemie (International ed. in English) · 2026Article
- Hydrogen Atom Transfer-Based C(spThe Journal of organic chemistry · 2025Article
- Direct stereoselective C(spNature chemistry · 2025Article
- Rapid prediction of conformationally-dependent DFT-level descriptors using graph neural networks for carboxylic acids and alkyl amines.Digital discovery · 2025Article
- Nickel/photoredox-catalyzed three-component silylacylation of acrylatesChemical science · 2024Article
- Nickel-catalysed enantioselective alkene dicarbofunctionalization enabled by photochemical aliphatic C-H bond activation.Nature catalysis · 2024Article
- Nickel-Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to α-Amino Ketones.Angewandte Chemie (International ed. in English) · 2023Article
- Oxidative Cross Dehydrogenative Coupling ofJournal of the American Chemical Society · 2023Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Site- and enantioselective cross-coupling of saturated N-heterocycles and carboxylic acids-two of the most abundant and versatile functionalities-to form pharmaceutically relevant α-acylated amine derivatives remains a major challenge in organic synthesis. Here, we report a general strategy for the highly site- and enantioselective α-acylation of saturated N-heterocycles with in situ-activated carboxylic acids. This modular approach exploits the hydrogen-atom-transfer reactivity of photocatalytically generated chlorine radicals in combination with asymmetric nickel catalysis to selectively functionalize cyclic α-amino C-H bonds in the presence of benzylic, allylic, acyclic α-amino, and α-oxy methylene groups. The mild and scalable protocol requires no organometallic reagents, displays excellent chemo-, site- and enantioselectivity, and is amenable to late-stage diversification, including a modular synthesis of previously inaccessible Taxol derivatives. Mechanistic studies highlight the exceptional versatility of the chiral nickel catalyst in orchestrating (i) catalytic chlorine elimination, (ii) alkyl radical capture, (iii) cross-coupling, and (iv) asymmetric induction.
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