Synthesis, structure, and catalytic properties of copper, palladium and cobalt complexes containing an N,O-type bidentate thiazoline ligand

Amini, Mojtaba; Bayrami, Arshad; Marashi, Mohammad Nazari; Arab, Ali; Ellern, Arkady; Woo, L. Keith

doi:10.1016/j.ica.2015.12.015

Cited by 36 publications

(14 citation statements)

References 31 publications

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“…1,3‐Cycloaddition reactions of azides with olefins provide direct access to a wide range of 1,2,3‐triazoles as useful heterocyclic systems with remarkably stable aromatic structures, which can serve, among other roles, as structural analogues of a peptide linkage . Copper catalysts accelerate the cycloaddition reactions of azides with such terminal alkynes by a factor of at least 106 relative to the uncatalysed case and copper‐catalysed azide–alkyne cycloaddition (CuAAC) is a well‐established methodology in modern organic synthesis …”

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confidence: 99%

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Amini

Nikkhoo

Farnia

2017

Applied Organom Chemis

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Readily prepared copper(II) immobilized on layered double hydroxide has been found to effectively catalyse the 1,3‐dipolar cycloaddition (CuAAC) of a variety terminal alkynes and benzyl azides generated in situ from sodium azide and benzyl halides furnishing the corresponding 1,2,3‐triazoles in excellent yields. The advantages of the protocol are short reaction time, mild reaction conditions, reusability of the catalyst and applicability to a wide range of substrates.

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confidence: 99%

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Amini

Nikkhoo

Farnia

2017

Applied Organom Chemis

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“…The catalytic activities for benzyl azide and phenylacetylene reactions of catalysts 1 and 2 have been compared with other reported Cu(I)‐based complexes (Table 4). [ 46,51–53 ] By comparing with [Cu(L1)(H 2 O) 2 ]·2H 2 O, 1 and 2 required a lower reaction temperature and a shorter reaction time. For the catalysts [Cu(L2) 2 ] and [Cu 2 (L3)(SiW 12 O 40 ) 0.5 ]·CH 3 CN·2H 2 O, 1 and 2 required a higher reaction temperature but a shorter reaction time.…”

Section: Resultsmentioning

confidence: 99%

Resorcin[4]arene‐based Cu(I) binuclear and mononuclear complexes as efficient catalysts for azide‐alkyne cycloaddition reactions

Qin

Liu

et al. 2021

Applied Organom Chemis

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In this study, three fascinating resorcin[4]arene‐based Cu(I) complexes, named [CuCl (TPC4R)] (1), [CuBr (TPC4R)] (2), and [Cu2I2(TPC4R)] (3) were prepared by using a pyrimidine‐functionalized resorcin[4]arene ligand (TPC4R). In 1 and 2, two Cu(I) ions were linked by two TPC4R and two Cl− (or Br−) anions to form binuclear units. The adjacent units were extended into supramolecular layers through H bonds. In 3, two Cu(I) ions were connected by one TPC4R and two I− anions to form a mononuclear complex. The mononuclear units were connected by hydrogen bonds to produce a supramolecular chain. Significantly, 1 and 2 exhibit high efficiency and universality for azide‐alkyne cycloaddition reactions in the synthesis 1,2,3‐triazoles and β‐OH‐1,2,3‐triazoles. It has been found that the amount of catalyst, solvent type and reaction temperature have considerable influences on the activities of catalytic systems. The conversions of catalysts 1 and 2 could reach 99% for most of the selected substrates. It was found that after repeatedly used for 4 times, the catalytic activity of 1 did not decrease apparently.

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“…However, recent publications have described the use of Cu(II) complexes as catalysts without the use of reducing agents. [113][114][115][116][117][118][119][120] Bagherzadeh et al 121 reported in 2019 the preparation of two Cu(II) complexes (Figure 6) and studied their catalytic potentials against the CuAAC reaction in the absence of reducing agents. The authors were able to prepare different 1H-1,2,3-triazole derivatives from a multicomponent reaction between benzyl chloride, sodium azide and different terminal alkynes with good yields.…”

Section: Main Sources Of Cu (Ii) Used In Cuaac Reactionsmentioning

confidence: 99%

1,2,3- Triazoles: general and key synthetic strategies

Santos¹,

Oliveira²,

Oliveira³

et al. 2020

Arkivoc

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The applications of the 1H-1,2,3-triazole derivatives are particularly attractive and have received prominent attention in scientific research. The characteristics of these heterocycles motivated the development of different strategies for their preparation and molecular diversification. Most of the synthetic procedures available in the literature are based on catalysis with copper salts. Therefore, this review has as complementary central focus and updates the information about the properties and the main methods for the preparation of 1H-1,2,3-triazole derivatives, with emphasis on methods involving 1,3-dipolar cycloaddition between organic azides and terminal alkynes catalyzed by copper.

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Synthesis, structure, and catalytic properties of copper, palladium and cobalt complexes containing an N,O-type bidentate thiazoline ligand

Cited by 36 publications

References 31 publications

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Synthesis, characterization and catalytic properties of tetrachlorocuprate(II) immobilized on layered double hydroxide

Resorcin[4]arene‐based Cu(I) binuclear and mononuclear complexes as efficient catalysts for azide‐alkyne cycloaddition reactions

1,2,3- Triazoles: general and key synthetic strategies

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