Synthesis and catalytic applications of C₃-symmetric tris(triazolyl)methanol ligands and derivatives

Abstract

Recently introduced tris(1,2,3-triazol-4-yl)methanols and derivatives (TTM ligands) have become a valuable subclass of C 3 -symmetric tripodal ligands for transition metal-mediated reactions. TTM-based ligand architectures are modularly constructed through regioselective, one-pot triple [3+2] cycloaddition of azides and alkynes. Applications of homogeneous systems of this type and of heterogenized (polystyrene-and magnetic nanoparticle-supported) TTM ligands in synthesis and catalysis are compiled in this Feature Article.

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

“…The use of microwaves was a valuable assistance in CuAAC reactions upon considerably shortening reaction times, and it improved yield [20,127c,165]. Perics's group reported the synthesis of tris(triazolyl)methane ligands [166] with CuCl for [167], recoverable and recyclable Cu/SiO 2 composite for eco-friendly multicomponent synthesis of 1,2,3-triazoles [168], "copper-in-charcoal" catalyzed triazole click reactions [169], palladium and copper-supported on charcoal as heterogeneous multi-task catalysts for sequential Sonogashira-click and click-Heck reactions [170], Cu/porous glass catalyst for CuAAC in water [165c], CuNPs supported on nano-Fe 3 O 4 -glutathione (Cu/nano-FGT) for one-pot multicomponent synthesis of 1,2,3-triazoles [171], and Fe 3 O 4 -supported CuBr catalysts for one-pot and scale-up synthesis of 1,2,3-triazoles (Fig. 32) [172].…”

Symmetrical Tertiary Amines: Applications and Synthetic Approaches

“…There are a lot of original research papers and reviews considering the synthesis and application of the tristriazolyl motif. [ 82–87 ]…”

Metal-based nanoparticles dispersed in glycerol: An efficient approach for catalysis

“…In contrast to the Cu(I) systems reported in the literature, no co-solvent was necessary to carry out this type of couplings [57,58]. Since the independent pioneering works from Sharpless [59] and Meldal [60], Cu(I)-based catalytic systems have been largely applied in Cu-catalyzed azide-alkyne cycloadditions (CuAAC) to afford 1,4-triazoles (selected reviews: [61][62][63][64][65][66]). Cu 2 ONPs in glycerol were efficient systems (isolated yields > 90%) for the reaction of benzylazide with different terminal alkynes including alkyl derivatives (Scheme 3a).…”