CAS 3023745-16-3, Cat. No EN300-52115571
Reagent for C1 homologation and C-H alkylation
(E)-Ethyl 2-(2-((4-(trifluoromethyl)phenyl)sulfonyl)hydrazono)acetate is a stable, crystalline reagent with excellent solubility in solvents like dichloromethane and THF. Its primary role as a radical acceptor in photocatalytic C(sp3)-C(sp3)1 bond formation allows for efficient and metal-free alkylation of C-H bonds, providing a milder alternative to traditional coupling methods. This reagent also supports the C1-homologation of carboxylic acids under visible light, enabling safer processes compared to the conventional Arndt-Eistert reaction2. Additionally, it has proven valuable for synthesizing β-arylethylamines and facilitating late-stage functionalization of peptides.
Synonyms: acetic acid, 2-[2-[[4-(trifluoromethyl)phenyl]sulfonyl]hydrazinylidene]-, ethyl ester
Selected publications
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Photocatalytic Alkylation of C(Sp3)−H Bonds Using Sulfonylhydrazones.
Pulcinella A.; Bonciolini S.; Lukas F.; Sorato A.; Noël T. Angewandte Chemie International Edition 2023, 62 (3). DOI: 10.1002/anie.202215374
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Metal-Free Photocatalytic Cross-Electrophile Coupling Enables C1 Homologation and Alkylation of Carboxylic Acids with Aldehydes.
Bonciolini S.; Pulcinella A.; Leone M.; Schiroli D.; Ruiz A.; Sorato A.; Dubois M.; Gopalakrishnan R.; Masson G.; Della Ca’ N.; Protti S.; Fagnoni M.; Zysman-Colman E.; Johansson M.; Noël T. Nat Commun 2024, 15 (1), 1509. DOI: 10.1038/s41467-024-45804-z