New Stable Cu(I) Catalyst Supported on Weakly Acidic
Polyacrylate Resin for “Click“Chemistry: Synthesis of
1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5- amine

J 2018

New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click“Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5- amine

KORE, Nitin Shivanna a Pavel PAZDERA

Základní údaje

Originální název

New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click“Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5- amine

Autoři

KORE, Nitin Shivanna (356 Indie, domácí) a Pavel PAZDERA (203 Česká republika, garant, domácí)

Vydání

Current Organic Synthesis, 2018, 1570-1794

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 1.841

Kód RIV

RIV/00216224:14310/18:00100661

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.2174/1570179415666180110152642

UT WoS

000435095700006

Klíčová slova anglicky

Polymer solid support; Supported Cu(I) catalyst; Click chemistry; Azide-Nitrile cycloaddition; Recyclable green catalyst; green process

Změněno: 23. 4. 2024 11:13, Mgr. Michal Petr

Anotace

V originále

Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene. Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds. Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic, and heterocyclic terminal alkynes and corresponding 1,4-disubstituted 1,2,3-triazoles were obtained almost in the quantitative yields. The cycloaddition reactions of aryl azide with nitriles consisting alpha-hydrogen on carbon attached to cyano group under catalytic action of the title supported Cu(I) ended up with the formation of 1,4- disubstituted 1,2,3-triazol-5-amines in quantitative yields. The title catalyst found to be active for nucleophilic substitution of aide group (-N3) to 4-Iodoanisole. Conclusion: It was found that both studied Azide-Alkyne cycloaddition and Azide-Nitrile cycloaddition syntheses are regioselective and quantitative in yield. The title catalyst used is economical, easily preparable, separable,and recyclable. Therefore, the studied syntheses may be regarded as environmentally clean and green processes.

Návaznosti

2A-1TP1/090, projekt VaV

Název: Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy.

Investor: Ministerstvo průmyslu a obchodu ČR, Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy

Citovat

KORE, Nitin Shivanna a Pavel PAZDERA. New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click“Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5- amine. Current Organic Synthesis. 2018, roč. 2018, č. 15, s. 1-14. ISSN 1570-1794. Dostupné z: https://dx.doi.org/10.2174/1570179415666180110152642.

@article{1413044,
   author = {Kore, Nitin Shivanna and Pazdera, Pavel},
   article_number = {15},
   doi = {http://dx.doi.org/10.2174/1570179415666180110152642},
   keywords = {Polymer solid support; Supported Cu(I) catalyst; Click chemistry; Azide-Nitrile cycloaddition; Recyclable green catalyst; green process},
   language = {eng},
   issn = {1570-1794},
   journal = {Current Organic Synthesis},
   title = {New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click“Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5- amine},
   url = {http://www.eurekaselect.com/158932/article},
   volume = {2018},
   year = {2018}
}

TY  - JOUR
ID  - 1413044
AU  - Kore, Nitin Shivanna - Pazdera, Pavel
PY  - 2018
TI  - New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click“Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5- amine
JF  - Current Organic Synthesis
VL  - 2018
IS  - 15
SP  - 1-14
EP  - 1-14
SN  - 15701794
KW  - Polymer solid support
KW  - Supported Cu(I) catalyst
KW  - Click chemistry
KW  - Azide-Nitrile cycloaddition
KW  - Recyclable green catalyst
KW  - green process
UR  - http://www.eurekaselect.com/158932/article
N2  - Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene. Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds. Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic, and heterocyclic terminal alkynes and corresponding 1,4-disubstituted 1,2,3-triazoles were obtained almost in the quantitative yields. The cycloaddition reactions of aryl azide with nitriles consisting alpha-hydrogen on carbon attached to cyano group under catalytic action of the title supported Cu(I) ended up with the formation of 1,4- disubstituted 1,2,3-triazol-5-amines in quantitative yields. The title catalyst found to be active for nucleophilic substitution of aide group (-N3) to 4-Iodoanisole. Conclusion: It was found that both studied Azide-Alkyne cycloaddition and Azide-Nitrile cycloaddition syntheses are regioselective and quantitative in yield. The title catalyst used is economical, easily preparable, separable,and recyclable. Therefore, the studied syntheses may be regarded as environmentally clean and green processes.
ER  -

KORE, Nitin Shivanna a Pavel PAZDERA. New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click“Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5- amine. \textit{Current Organic Synthesis}. 2018, roč.~2018, č.~15, s.~1-14. ISSN~1570-1794. Dostupné z: https://dx.doi.org/10.2174/1570179415666180110152642.

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