{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,24]],"date-time":"2026-01-24T10:11:44Z","timestamp":1769249504997,"version":"3.49.0"},"reference-count":72,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2022,2,25]],"date-time":"2022-02-25T00:00:00Z","timestamp":1645747200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"abstract":"<jats:p>Time-dependent monitoring of the reactive intermediates provides valuable information about the mechanism of a synthetic transformation. However, the process frequently involves intermediates with short lifetimes that significantly challenge the accessibility of the desired kinetic data. We report <jats:italic>in situ<\/jats:italic> cyclic voltammetry (CV) and nuclear magnetic resonance (NMR) spectroscopy studies of the cycloaddition reaction of organobismuth(III) compounds with organic azides under the copper(I)-catalyzed conditions. A series of bismuth(III) acetylides carrying diphenyl sulfone scaffolds have been synthesized to study the underlying electronic and steric effects of the tethered moieties capable of transannular oxygen O\u00b7\u00b7\u00b7Bi interactions and <jats:italic>para<\/jats:italic>-functionality of the parent phenylacetylene backbones. While belonging to the family of copper-catalyzed azide-alkyne cycloaddition reactions, the reaction yielding 5-bismuth(III)-triazolide is the sole example of a complex catalytic transformation that features activity of bismuth(III) acetylides towards organic azides under copper(I)-catalyzed conditions. Stepwise continuous monitoring of the copper(I)\/copper(0) redox activity of the copper(I) catalyst by cyclic voltammetry provided novel insights into the complex catalytic cycle of the bismuth(III)-triazolide formation. From CV-derived kinetic data, reaction rate parameters of the bismuth(III) acetylides coordination to the copper(I) catalyst (K<jats:sub>A<\/jats:sub>) and equilibrium concentration of the copper species [cat]<jats:sub>eq.<\/jats:sub> are compared with the overall 5-bismuth(III)-triazolide formation rate constant k<jats:sub>obs<\/jats:sub> obtained by <jats:sup>1<\/jats:sup>H-NMR kinetic analysis.<\/jats:p>","DOI":"10.3389\/fchem.2022.830237","type":"journal-article","created":{"date-parts":[[2022,2,25]],"date-time":"2022-02-25T10:04:45Z","timestamp":1645783485000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":3,"title":["Electrochemical Studies of the Cycloaddition Activity of Bismuth(III) Acetylides Towards Organic Azides Under Copper(I)-Catalyzed Conditions"],"prefix":"10.3389","volume":"10","author":[{"given":"Antonina L.","family":"Nazarova","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Billal","family":"Zayat","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Valery V.","family":"Fokin","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sri R.","family":"Narayan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1965","published-online":{"date-parts":[[2022,2,25]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"3039","DOI":"10.1016\/s0040-4020(01)85938-x","article-title":"Newer Methods of Arylation","volume":"44","author":"Abramovitch","year":"1988","journal-title":"Tetrahedron"},{"key":"B2","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1007\/978-1-4419-9276-5_2","article-title":"Chemical Kinetics and Reaction Mechanisms","volume-title":"Chemical Kinetics and Inorganic Reaction Mechanisms","author":"A\u0161perger","year":"2003"},{"key":"B3","doi-asserted-by":"publisher","first-page":"937","DOI":"10.1351\/pac198759080937","article-title":"Bismuth(V) Reagents in Organic Synthesis","volume":"59","author":"Barton","year":"1987","journal-title":"Pure Appl. 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