First synthesis of both 1-aryl-4-[(E)-alk-1-enyl]-1H-1,2,3-triazoles and 1-aryl-4-[(Z)-1-(trimethylsilyl)alk-1-enyl]-1H-1,2,3-triazoles: assembly of π-extended 1,2,3-triazoles using a cross-coupling/click reaction sequence

Triazole‐Functionalized Norbornadiene‐Quadricyclane Photoswitches for Solar Energy Storage

“…As there was a necessity to have deprotected alkynes in the reactions forming triazole products, two different methods were used for the CuAAC reaction, which avoided the isolation of potentially unstable neat terminal acetylenes. This included a previously reported in situ deprotection using sodium methoxide in the presence of catalytic amounts of copper acetate and sodium ascorbate . The other method entailed deprotection using potassium carbonate and following a work up procedure which avoided concentration of the terminal alkynes, and subjecting a toluene solution of NBD7 and NBD8 into the next step under standard CuAAC reaction conditions of cuprous iodide and Hünig's base.…”

[3+2]‐Cycloaddition for Fully Decorated Vinyl‐1,2,3‐Triazoles: Design, Synthesis and Applications

“…[11] In 2016, Hoshi et al reported a route for one-pot two-step synthesis of β-substituted 4-vinyl-1,2,3-triazoles via a sequence of cross-coupling followed by CuAAC. [12] The intermediate, terminal conjugated (E)-enynes 24 resulting from Cu(acac) 2catalyzed cross-coupling reaction of (E)-alk-1-enyldisiamylboranes 23 with (trimethylsilyl)ethynyl bromide 22 in 1.0 M NaOMe solution, underwent CuAAC with the aryl azides 20, prepared from arylboronic acids (1.0 equiv.) and sodium azide (1.5 equiv.)…”

“…catalysed by Cu(OAc) 2 in another flask, on further addition of NaASc and furnished the corresponding products 25 in 41-74% yields (Scheme 7). [12] In 2018, Qin and co-workers explored an efficient sequential protocol for the synthesis of β-substituted 4-vinyl-1,2,3-triazoles via a SO 2 F 2 -promoted dehydration and dehydrogenation process. [13] In this process, the intermediate, terminal conjugated (E)-enynes 24 were resulted from the corresponding 2vinyl alcohol 26, which reacted with SO 2 F 2 in DMSO solvent in the presence of K 2 CO 3 basic medium, to initially provide the carbonyl compounds following Swern-oxidation like pathway, and further reaction of (10 mol%) and NaASc (10 mol%) in DMSO:H 2 O (1 : 1) mixture at 25°C for 12 h furnished the desired product 4-VT 25 in 53% overall yield (Scheme 8).…”