Related Experiment Video
Updated: Jul 25, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Carboamination and olefination: ortho C-H functionalization of phenoxyacetamide
Tanmayee Nanda1,2, Shubham Kumar Dhal1,2, Gopal Krushna Das Adhikari1,2
1School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar, Odisha 752050, India. pcr@niser.ac.in.
Abstract:
Herein, we have demonstrated a rhodium-catalyzed carboamination of olefin with the double bond intact. For the first time, deacylative carboamination of the maleimide has been achieved wherein phenoxyacetamide has behaved as the aminating source. In addition to carboamination, we have also disclosed the C-H olefination protocol where the maleimide group has been installed successfully in the ortho-position of phenoxyacetamide. In this protocol, phenoxyacetamide behaved as a traceless directing group with the in situ release of acetamide. The base-assisted E2-elimination is the key to the success of the olefination reaction.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives
Preparation of Carboxylic Acids: Hydrolysis of Nitriles