Related Experiment Video
Updated: Sep 29, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines
Pavel A Sakharov1, Mikhail S Novikov1, Tuan K Nguyen1
1St. Petersburg State University, Institute of Chemistry, 7/9 Universitetskaya nab, St. Petersburg 199034, Russia.
Abstract:
A metal-free scalable synthesis of functionalized ketenimines from alkyl α-(aryl/heteroaryl)-α-diazoacetates and alkyl isocyanides induced by blue light irradiation has been developed. The reaction proceeds at room temperature without any photocatalyst and provides ketenimines in moderate to good yields. Density functional theory (DFT) calculations and the experimental study showed that aryl(alkoxycarbonyl)carbenes in both singlet and triplet states can react with isocyanides but only the reaction of the former leads to the smooth formation of ketenimines. The obtained ketenimines were used for the synthesis of functionalized amidines under mild metal-free conditions.
More Related Videos
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
Related Concept Videos
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Aldol Condensation with β-Diesters: Knoevenagel Condensation
α-Alkylation of Ketones via Enolate Ions
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis