Related Experiment Video
Updated: Mar 31, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Direct C-H Bond Arylation of Thienyl Thioamides Catalyzed by Pd-Phenanthroline Complexes
Takayuki Yamauchi1, Fumitoshi Shibahara1, Toshiaki Murai1,2
1Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University , Yanagido, Gifu 501-1193, Japan.
Abstract:
A direct C-H bond arylation method for thienyl thioamides catalyzed by [Pd(phen)2](PF6)2 was developed. This reaction selectively afforded 2-monoarylated products, while the corresponding amide thiophene derivatives furnished 2,5-diarylated products. Mechanistic studies revealed that a Pd(II)-bisthioamide complex should be the active species for the reaction of thienyl thioamides in the presence of catalytic amounts of [Pd(phen)2](PF6)2. Similar to the reaction with amides, the reaction with thioamides selectively generated the 2,5-diarylated products when a preformed Pd(phen)PhI complex was used.
Related Concept Videos
Diazonium Group Substitution: –OH and –H
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Nucleophilic Aromatic Substitution: Elimination–Addition
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
