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Updated: Dec 18, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Process-Controlled Regiodivergent Copper-Catalyzed Azide-Alkyne Cycloadditions: Tailor-made Syntheses of 4- and
Abstract:
We developed a regiodivergent syntheses of 4- and 5-bromo-substituted 1,2,3-triazoles in copper-catalyzed azide-alkyne cycloadditions (CuAACs) by taking advantage of bromo(phosphoryl)ethyne 1 as a bromoethyne equivalent. A one-shot dephosphorylative CuAAC of 1 afforded 4-bromotriazoles, which was transformed into a histone deacetylase 8 (HDAC8)-selective inhibitor, NCC-149. However, the direct CuAAC catalyzed by CuI/Cu(OAc)2 provided 5-bromo-4-phosphoryltriazoles. The consecutive nucleophilic substitution of the bromo group with thiols followed by MeOK-promoted dephosphorylation gave 5-thio-substituted triazoles.
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