Synthesis of 1-arylsulfonyl-1,2,3-triazoles from (Z)-arylvinyl bromides by sequential elimination–cycloaddition reaction

Zhang, Wensheng; Xu, Wenjing

doi:10.1007/s10593-016-1859-x

Cited by 5 publications

(1 citation statement)

References 33 publications

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“…In 2016, Zhang and co-workers reported the synthesis of 4-substituted N -sulfonyl-1,2,3-triazoles 9.3 from ( Z )-arylvinyl bromides 9.1 and sulfonyl azides (Scheme ). The synthesis was accomplished through sequential KOH-promoted HBr elimination from the vinyl bromide and copper-catalyzed [3 + 2] cycloaddition of the resulting alkyne 9.2 with azide.…”

Section: Synthesis Of 123-triazolesmentioning

confidence: 99%

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

2022

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Readily accessible and shelf-stable 1,2,3-triazole and its analogues such as pyridotriazole, triazoloindole, benzotriazole, and thiadiazole exist in equilibrium with their ring-opened isomers, viz., diazo compounds. These ring-opened isomers could be trapped by various metal catalysts (e.g., Rh, Pd, Cu, Co, Ag, etc.) to generate the corresponding metal carbenoids with extrusion of nitrogen. As a consequence, these unique N-heterocycles facilitate access to a realm of N-containing complex structural motifs of biological importance through denitrogenative transformations such as transannulations, insertions, ylide formation, and rearrangements by trapping of the metal carbenoids with a diverse range of coupling partners (e.g., alkenes, alkynes, nitriles, carbo/heterocycles, X–H/C–X bonds, etc.). Hence, suitably substituted triazole derivatives have emerged as efficient surrogates of diazo compounds for the generation of reactive metal carbenoids during the past decades. In this comprehensive review, we aim to discuss in detail the remarkable advancement in their synthesis and synthetic applications.

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Section: Synthesis Of 123-triazolesmentioning

confidence: 99%