Related Experiment Video
Updated: Sep 6, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium-Catalyzed 1,2-Carboamination of Acrylamides via Anti-Michael-Type Addition
Sumit Singh1, Masilamani Jeganmohan1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai600036, Tamil Nadu, India.
Abstract:
Herein, we report a palladium-catalyzed 1,2-carboamination of acrylamides via anti-Michael-type addition. The protocol enables reverse regioselective functionalization of activated alkenes using carbazole derivatives as nucleophiles and aryl, vinyl, and alkyl iodide derivatives as electrophiles under mild reaction conditions. The three-component carboamination reaction proceeds via the simultaneous formation of C-C and C-N bonds, furnishing structurally diverse carboaminated products in moderate to excellent yields, with broad substrate scope and functional-group tolerance. Preliminary mechanistic studies suggest directed alkene activation by Pd(II), followed by anti-nucleopalladation to generate a proposed alkyl-Pd(II) intermediate, which subsequently undergoes coupling with aryl iodides to furnish the desired products. This work expands the scope of anti-Michael-type alkene functionalization and provides efficient access to structurally diverse nitrogen-containing molecules.
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Conjugate Addition of Enolates: Michael Addition
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Anionic Chain-Growth Polymerization: Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane