Regioselective Zn(OAc)2-catalyzed azide–alkyne cycloaddition in water: the green click-chemistry

文献情報

出版日 2017-02-08

DOI 10.1039/C6QO00787B

インパクトファクター 5.281

著者

Maria A. Morozova, Mekhman S. Yusubov, Václav Eigner, Alexander A. Bondarev, Akio Saito, Marina E. Trusova, Pavel S. Postnikov

原文を見る

要旨

A new method of azide–alkyne cycloaddition (AAC) in the presence of Zn(OAc)2 as an inexpensive and environmentally friendly catalyst in neat water has been developed. The proposed methodology has been applied for the synthesis of 1,4-disubstituted-1,2,3-triazoles from terminal alkynes and 1,4,5-trisubstituted-1,2,3-triazoles from internal alkynes. It has been found that Zn-catalyzed AAC is extremely sensitive to steric hindrance in acetylenes and a method of regioselective triazole ring formation has been proposed. Particularly important is the isolation and characterization of a relatively stable Zn-containing intermediate, which has been characterized by NMR and HRMS.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Regioselective Zn(OAc)2-catalyzed azide–alkyne cycloaddition in water: the green click-chemistry

文献情報

おすすめジャーナル

関連文献

Solvation properties of protic ionic liquids and molecular solvents

Inside back cover

Theoretical insights into the effect of the overpotential on CO electroreduction mechanisms on Cu(111): regulation and application of electrode potentials from a CO coverage-dependent electrochemical model

Onset of ionic coherence and ultrafast charge dynamics in attosecond molecular ionisation

Solvation dynamics: improved reproduction of the time-dependent Stokes shift with polarizable empirical force field chromophore models

Ultrafast X-ray photoelectron diffraction in triatomic molecules by circularly polarized attosecond light pulses

Spontaneous proton transfer in a series of amphoteric molecules under hydrostatic pressure

Atomically dispersed platinum on low index and stepped ceria surfaces: phase diagrams and stability analysis

Theoretical investigation of the valence states in Au via the Au–F compounds under high pressure

Minimization of solid-state conformational disorder in donor–acceptor TADF compounds

こちらもおすすめ

4-アミノフェノール酸ナトリウム水和物とは何ですか？

Methyl 3-methyl-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-histidinateの代替品はありますか？

4-Boc-2-哌嗪甲酸の市場動向や研究トレンドはどうですか？

4,4'-二羟甲基联苯の物理化学的性質は何ですか？

5-甲硫基戊腈はどの業界で使用されていますか？

CAS番号1311961-50-8の化合物はどのように合成されますか？

6-ブロモベンジジミダゾール-2-カルビルデオキシドはどのように保存すればよいですか？

Boc-N-甲基氨甲环酸とは何ですか？

乙基三氟硼酸钾はどのように合成されますか？

2-フロウロ-5-クロロ-4-アミノフェノールはどのように保存すればよいですか？

掲載誌

Organic Chemistry Frontiers

おすすめ化合物

(S)-3-((tert-Butoxycarbonyl)amino)-4-(4-(tert-butyl)phenyl)butanoic acid

6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid

Methyl 3-({2'-[(E)-(hydroxyhydrazono)methyl]-4-biphenylyl}methyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine

4-Biphenylyl(chloro)dimethylsilane

おすすめサプライヤー