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Synthesis of 5-Iodo-1,2,3-triazoles from Organic Azides and Terminal Alkynes

Title: Synthesis of 5-Iodo-1,2,3-triazoles from Organic Azides and Terminal Alkynes: Ligand Acceleration Effect, Substrate Scope, and Mechanistic Insights.
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Name(s): Zhu, Lei, 1978-, author
Barsoum, David, author
Brassard, Christopher, author
Deeb, Jason, author
Okashah, Najeah, author
Sreenath, Kesavapillai, author
Simmons, J., author
Type of Resource: text
Genre: Text
Issuance: serial
Date Issued: 2013
Physical Form: computer
online resource
Extent: 1 online resource
Language(s): English
Abstract/Description: An improved method has been developed for the preparation of 5-iodo-1,2,3-triazoles directly from organic azides and terminal alkynes by a reaction mediated by copper(I) and iodinating agents generated in situ. The major methodological advance of the current procedure is that it provides a high conversion and good iodo/proto selectivity with a broad range of substrates without using an excess of the alkyne, which was required in the previous method. The use of an accelerating ligand is essential to the success of reactions involving unreactive azides or alkynes. New mechanistic insights are provided, including the confirmation that a 1-iodoalkyne is formed as a key intermediate under the established conditions for the reaction.
Identifier: FSU_migr_chm_faculty_publications-0014 (IID), 10.1055/s-0033-1339312 (DOI)
Keywords: iodotriazole, triiodide, iodoalkyne, copper, TBTA, organic azide
Citation: "Synthesis of 5-Iodo-1,2,3-triazoles from Organic Azides and Terminal Alkynes: Ligand Acceleration Effect, Substrate Scope, and Mechanistic Insights" Barsoum, D. N.; Brassard, C. J.; Deeb, J. H. A.; Okashah, N.; Sreenath, K.; Simmons, J. T.; Zhu, L. Synthesis. 2013, 45, 2372–2386.
Subject(s): Chemistry, Inorganic
Chemistry, Organic
Links: http://dx.doi.org/10.1055/s-0033-1339312
Persistent Link to This Record: http://purl.flvc.org/fsu/fd/FSU_migr_chm_faculty_publications-0014
Owner Institution: FSU
Is Part of Series: Department of Chemistry and Biochemistry Faculty Publications.
Is Part Of: Synthesis.
Issue: 17, 45

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Zhu, L., Barsoum, D., Brassard, C., Deeb, J., Okashah, N., Sreenath, K., & Simmons, J. (2013). Synthesis of 5-Iodo-1,2,3-triazoles from Organic Azides and Terminal Alkynes: Ligand Acceleration Effect, Substrate Scope, and Mechanistic Insights. Synthesis. Retrieved from http://dx.doi.org/10.1055/s-0033-1339312