Related Experiment Video
Updated: Jul 20, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
NbCl5-catalyzed sulfa-Michael addition for constructing quaternary centers in enones
Mingxia Ye1, Yingying Xu1, Tianhang Song2
1Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing, Jiangsu, China. zgao@njau.edu.cn.
Abstract:
A novel NbCl5-catalyzed sulfa-conjugate addition has been developed to construct quaternary centers in various enones. This new method enables a range of functionalized thiols to access different β-sulfido carbonyl compounds bearing a quaternary center. 27 novel β-sulfido ketones have been obtained with moderate to excellent yields. The preparative scale reactions also proceed well, showing no decrease in yield. We further studied the mechanism by DFT calculations. This methodology is significant in sulfur chemistry, especially in sulfa-conjugate addition, giving a new pathway to add thiols to tri-substituted enones.
More Related Videos
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Conjugate Addition of Enolates: Michael Addition
Nucleophilic Aromatic Substitution: Elimination–Addition
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Radical Anti-Markovnikov Addition to Alkenes: Overview
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Preparation and Reactions of Sulfides