Related Experiment Video
Updated: Sep 6, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-Catalyzed Sulfinamidation of Aryl Chlorides
Ming-Kai Wei1, Michael C Willis1
1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, OxfordOX1 3TA, U.K.
Abstract:
The transition-metal-catalyzed addition of aryl halides to N-sulfinylamines is a valuable method for the synthesis of aza-sulfur functional groups. However, to date, the substrate scope has been limited to aryl iodides and bromides. Here, we report the Pd-catalyzed sulfinamidation of aryl chlorides using sulfinylamine reagent TIPS-NSO, which exploits the lower cost, greater commercial availability, and broader structural diversity of aryl chloride substrates. The reaction tolerates a broad range of (hetero)aryl chloride substrates, including pharmaceutically relevant examples. The Pd loading can be reduced to 2.5 mol %, and the reactions can be conducted on a gram scale.
Related Concept Videos
Preparation and Reactions of Sulfides
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Electrophilic Aromatic Substitution: Sulfonation of Benzene
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)