Synthesis of adamantyl substituted 1,2,3-triazol-5-ylidene ligands and their PEPPSI-type palladium complexes

Suzuki–Miyaura and Hiyama coupling catalyzed by PEPPSI-type complexes with non-bulky NHC ligand

“…In contrast, their applications in the Hiyama coupling are rather scarce [25][26][27]. This is surprising because these two methods, the Suzuki-Miyaura and the Hiyama reactions, present alternative pathways leading to biaryl compounds and, therefore, it could be interesting to estimate their relative applicability under similar reaction conditions.…”

Magnetite tethered mesoionic carbene‐palladium (II): An efficient and reusable nanomagnetic catalyst for Suzuki‐Miyaura and Mizoroki‐Heck cross‐coupling reactions in aqueous medium

“…Therefore, various types of catalysts have been developed for Suzuki–Miyaura and Mizoroki‐Heck cross‐coupling reactions. Among these, 1,3,4‐trisubstituted 1,2,3‐triazol‐5‐ylidene metal complexes have shown tremendous catalytic activities and various homogeneous catalysts have been developed . However, the major disadvantages of homogeneous catalysts include difficulty of their recovery from the reaction medium for reuse.…”

“…Among these, 1,3,4-trisubstituted 1,2,3-triazol-5-ylidene metal complexes have shown tremendous catalytic activities and various homogeneous catalysts have been developed. [19,[33][34][35][36] However, the major disadvantages of homogeneous catalysts include difficulty of their recovery from the reaction medium for reuse. This problem is of economic and environmental concern in bulk synthesis.…”

Synthesis of the First Resorcin[4]arene-Functionalized Triazolium Salts and Their Use in Suzuki–Miyaura Cross-Coupling Reactions

“…Their precursors, namely 1,2,3-triazoles, are easily accessible through copper-catalyzed Huisgen [3 + 2] click-type cycloaddition of azides and alkynes (CuAAC) [6,7], followed by N3-quaternarization. The resulting 1,2,3-triazolium salts can then be converted to transition metal complexes that, i.a., are suitable for Suzuki-Miyaura [8][9][10][11][12][13][14][15][16][17][18], Mizoroki-Heck [19,20], and Sonogashira coupling reactions [19,21], as well as for various reduction or oxidation reactions [22][23][24][25][26][27], and C-heteroatom bond forming reactions [28][29][30][31][32].…”

“…Synthesis of 1,4-bis{4(24),6(10),12(16),18(22)-Tetramethylenedioxy-2,8,14,20-tetrapentylresorcin[4]arene-5-yl}-1H-1,2,3-triazole(8) A solution of ethynyl-cavitand 5 (0.490 g, 0.58 mmol), azido-cavitand 6 (0.500 g, 0.58 mmol), CuSO 4 •5H 2 O (0.014 g, 0.06 mmol), and sodium ascorbate (0.012 g, 0.06 mmol) in DMF (50 mL) was stirred for 36 h at 100 • C. Afterwards, the mixture was cooled to room temperature and evaporated to dryness. The resulting residue was dissolved in CH 2 Cl 2 (200 mL).…”