1,2,3-Triazol-5-ylidene–palladium complex catalyzed Mizoroki–Heck and Sonogashira coupling reactions

• Published in: Tetrahedron Vol. 67; no. 38; pp. 7263 - 7267
• Main Authors: Inomata, Sayuri, Hiroki, Hidekatsu, Terashima, Takahiro, Ogata, Kenichi, Fukuzawa, Shin-ichi
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 23.09.2011; Elsevier
• Subjects: 1,2,3-Triazole; Alkenes; Alkynes; Analogue; Aromatic compounds; Bromides; Catalysis; Catalysts: preparations and properties; Chemical reactions; Chemistry; Chlorides; Cross coupling; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; N-Heterocyclic carbene; Organic chemistry; Palladium; Preparations and properties; Tetrahedrons; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Cross coupling; Palladium; 1,2,3-Triazole; Catalysis; N-Heterocyclic carbene; Catalytic reaction; Acetylenic compound; Haloarene; Heck reaction; Palladium complex; Transition metal; Transition metal Complexes; Ylidene complex; Chemical coupling; Sonogashira coupling; Alkene; Functionalization; Cross reaction; Platinoid Complexes; Platinoid; Ethylenic compound; Alkyne; Halogen Organic compounds
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.07.045

The bis-1,4-dimesityl-1,2,3-triazol-5-ylidene–palladium complex ( 1a) successfully catalyzes the Mizoroki–Heck and Sonogashira coupling reactions with aryl bromides to give the corresponding alkenes and alkynes, respectively, in good to excellent yields. In the Mizoroki–Heck reaction, electron-rich, electron-poor, and functionalized aryl bromides and alkenes are tolerated, while the substrates are limited to electron-poor aryl halides in the Sonogashira coupling reaction. The palladium complex also catalyzes cross-coupling reactions with aryl chlorides to give higher yields of products than does the bis-IMes–Pd complex analogue ( 2), under specific conditions. [Display omitted]