A recyclable and efficient triazole ligand for the palladium-catalyzed Suzuki–Miyaura and Mizoroki–Heck reactions

• Published in: Catalysis communications Vol. 15; no. 1; pp. 118 - 122
• Main Authors: Zhu, Yi-Wei, Yi, Wen-Bin, Cai, Chun
• Format: Journal Article
• Language: English
• Published: AMSTERDAM Elsevier B.V 15.11.2011; Elsevier
• Subjects: [1,2,3]-triazole; Chemistry; Chemistry, Physical; Coupling reactions; F-SPE (fluorous solid–phase extraction); Fluorous ligand; Palladium; Physical Sciences; Science & Technology; Palladium; Fluorous ligand; Coupling reactions; F-SPE (fluorous solid–phase extraction); [1,2,3]-triazole; COMPLEXES SYNTHESIS; SONOGASHIRA; F-SPE (fluorous solid-phase extraction); BROMIDES; ARYL CHLORIDES; SOLID-PHASE EXTRACTION; PYRIDINE CATALYST
• ISSN: 1566-7367; 1873-3905
• DOI: 10.1016/j.catcom.2011.08.023

A new fluoroalkylated 1,4-disubstituted [1,2,3]-triazole was prepared and acted as an efficient ligand in the palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl boronic acids and aryl halides (Ar–Br and Ar–Cl) and Mizoroki–Heck reactions of aryl halides and alkenes. All reactions proceeded smoothly to give the desired products in moderate to excellent yields under the optimal conditions. Moreover, the ligand could be easily recovered by fluorous solid-phase extraction with excellent purity and reused with slightly decrease in its activity. [Display omitted] ► A new fluorous triazole ligand was synthesized. ► It displayed excellent catalytic performance in coupling reactions with Pd(OAc) 2. ► It could be easily recovered by fluorous solid-phase extraction with good purity. ► It could be reused with slightly decrease in its activity.