An Atom-Economic Method for 1,2,3-Triazole Derivatives via Oxidative [3 + 2] Cycloaddition Harnessing the Power of Electrochemical Oxidation and Click Chemistry

Abstract

An electrochemical method was developed to accomplish the reagentless synthesis of 4,5-disubstituted triazole derivatives employing secondary propargyl alcohol as C-3 synthon and sodium azide as cycloaddition counterpart. The reaction was conducted at room temperature in an undivided cell with a constant current using a pencil graphite (C) anode and stainless-steel cathode in a MeCN solvent system. The proposed reaction mechanism was convincingly established by carrying out a series of control experiments and further supported by electrochemical and density functional theory (DFT) studies.

Recent Advances in Radical Transformations of Propargylic Alcohols

“…In 2023, Bera's group [34] developed an electrochemical strategy to accomplish oxidative [3 + 3] cycloaddition of secondary propargylic alcohols 6 with sodium azide for the synthesis of various 4,5disubstituted triazoles 62 in the presence of n-Bu 4 NI as a supporting electrolyte (Scheme 24). Both aryl-and alkyl-substituted propargylic alcohols were compatible with this transformation, smoothly affording a series of 4,5-disubstituted triazoles in moderate to good yields.…”

Copper-catalyzed remote nucleophilic substitution of 5-ethynylthiophene esters

“…3 On the other hand, metal–acetylide complexes are valuable synthetic intermediates that can be readily prepared from terminal alkynes via metal activation. They can undergo [3 + 2] annulation, 4 the Kinugasa reaction 5 and alkyne–azide cycloaddition, 6 providing complex molecular frameworks (Fig. 1a-II).…”