1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: a One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles

Anastasia I. Govdi, Natalia A. Danilkina, Alexander V. Ponomarev, Irina A. Balova

Research output

1 Citation (Scopus)

Abstract

Cu-catalyzed 1,3-dipolar cycloaddition of iododiacetylenes with organic azides using iodotris(triphenylphosphine)copper(I) as a catalyst was found to be an efficient one-step synthetic route to 5-iodo-4-ethynyltriazoles. The reaction is tolerant to various functional groups in both butadiyne and azide moieties. The synthetic application of 5-iodo-4-ethynyl triazoles obtained was also evaluated: the Sonogashira coupling with alkynes resulted in unsymmetrically substituted triazole-fused enediyne systems, while the Suzuki reaction yielded the corresponding 5-aryl-4-ethynyl triazoles.

Original languageEnglish
Pages (from-to)1925-1940
Number of pages16
JournalJournal of Organic Chemistry
Volume84
Issue number4
DOIs
Publication statusPublished - 15 Feb 2019

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Diynes
Triazoles
Alkynes
Azides
Cycloaddition
Copper
Enediynes
Functional groups
Catalysts
5-iodo-1,2,3-triazole

Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry

Cite this

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title = "1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: a One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles",
abstract = "Cu-catalyzed 1,3-dipolar cycloaddition of iododiacetylenes with organic azides using iodotris(triphenylphosphine)copper(I) as a catalyst was found to be an efficient one-step synthetic route to 5-iodo-4-ethynyltriazoles. The reaction is tolerant to various functional groups in both butadiyne and azide moieties. The synthetic application of 5-iodo-4-ethynyl triazoles obtained was also evaluated: the Sonogashira coupling with alkynes resulted in unsymmetrically substituted triazole-fused enediyne systems, while the Suzuki reaction yielded the corresponding 5-aryl-4-ethynyl triazoles.",
keywords = "ONE-POT SYNTHESIS, CLICK-CHEMISTRY, REGIOSELECTIVE SYNTHESIS, COUPLING REACTION, 1,4,5-TRISUBSTITUTED 1,2,3-TRIAZOLES, SUBSTITUTED 1,2,3-TRIAZOLES, ELECTROPHILIC CYCLIZATION, CONVENIENT SYNTHESIS, TERMINAL ALKYNES, ACID CATALYSIS",
author = "Govdi, {Anastasia I.} and Danilkina, {Natalia A.} and Ponomarev, {Alexander V.} and Balova, {Irina A.}",
year = "2019",
month = "2",
day = "15",
doi = "10.1021/acs.joc.8b02916",
language = "English",
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pages = "1925--1940",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
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T1 - 1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: a One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles

AU - Govdi, Anastasia I.

AU - Danilkina, Natalia A.

AU - Ponomarev, Alexander V.

AU - Balova, Irina A.

PY - 2019/2/15

Y1 - 2019/2/15

N2 - Cu-catalyzed 1,3-dipolar cycloaddition of iododiacetylenes with organic azides using iodotris(triphenylphosphine)copper(I) as a catalyst was found to be an efficient one-step synthetic route to 5-iodo-4-ethynyltriazoles. The reaction is tolerant to various functional groups in both butadiyne and azide moieties. The synthetic application of 5-iodo-4-ethynyl triazoles obtained was also evaluated: the Sonogashira coupling with alkynes resulted in unsymmetrically substituted triazole-fused enediyne systems, while the Suzuki reaction yielded the corresponding 5-aryl-4-ethynyl triazoles.

AB - Cu-catalyzed 1,3-dipolar cycloaddition of iododiacetylenes with organic azides using iodotris(triphenylphosphine)copper(I) as a catalyst was found to be an efficient one-step synthetic route to 5-iodo-4-ethynyltriazoles. The reaction is tolerant to various functional groups in both butadiyne and azide moieties. The synthetic application of 5-iodo-4-ethynyl triazoles obtained was also evaluated: the Sonogashira coupling with alkynes resulted in unsymmetrically substituted triazole-fused enediyne systems, while the Suzuki reaction yielded the corresponding 5-aryl-4-ethynyl triazoles.

KW - ONE-POT SYNTHESIS

KW - CLICK-CHEMISTRY

KW - REGIOSELECTIVE SYNTHESIS

KW - COUPLING REACTION

KW - 1,4,5-TRISUBSTITUTED 1,2,3-TRIAZOLES

KW - SUBSTITUTED 1,2,3-TRIAZOLES

KW - ELECTROPHILIC CYCLIZATION

KW - CONVENIENT SYNTHESIS

KW - TERMINAL ALKYNES

KW - ACID CATALYSIS

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UR - http://www.mendeley.com/research/1iodobuta13diynes-coppercatalyzed-azidealkyne-cycloaddition-onestep-route-4ethynyl5iodo123triazoles

U2 - 10.1021/acs.joc.8b02916

DO - 10.1021/acs.joc.8b02916

M3 - Article

VL - 84

SP - 1925

EP - 1940

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

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