Standard

1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: a One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles. / Govdi, Anastasia I. ; Danilkina, Natalia A. ; Ponomarev, Alexander V. ; Balova, Irina A. .

In: Journal of Organic Chemistry, Vol. 84, No. 4, 15.02.2019, p. 1925-1940.

Research output: Contribution to journal › Article › peer-review

Harvard

Govdi, AI, Danilkina, NA, Ponomarev, AV & Balova, IA 2019, '1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: a One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles', Journal of Organic Chemistry, vol. 84, no. 4, pp. 1925-1940. https://doi.org/10.1021/acs.joc.8b02916

APA

Govdi, A. I., Danilkina, N. A., Ponomarev, A. V., & Balova, I. A. (2019). 1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: a One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles. Journal of Organic Chemistry, 84(4), 1925-1940. https://doi.org/10.1021/acs.joc.8b02916

Vancouver

Govdi AI, Danilkina NA, Ponomarev AV, Balova IA. 1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: a One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles. Journal of Organic Chemistry. 2019 Feb 15;84(4):1925-1940. https://doi.org/10.1021/acs.joc.8b02916

Author

Govdi, Anastasia I. ; Danilkina, Natalia A. ; Ponomarev, Alexander V. ; Balova, Irina A. . / 1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: a One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 4. pp. 1925-1940.

BibTeX

@article{d74e484edd9347bbbdcd769975f9f6e3,
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 = feb,
day = "15",
doi = "10.1021/acs.joc.8b02916",
language = "English",
volume = "84",
pages = "1925--1940",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "4",

}

RIS

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=85061262040&partnerID=8YFLogxK

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

IS - 4

ER -

ID: 39224187