Literature DB >> 19775097

A highly active catalyst for Huisgen 1,3-dipolar cycloadditions based on the tris(triazolyl)methanol-Cu(I) structure.

Salih Ozçubukçu1, Erhan Ozkal, Ciril Jimeno, Miquel A Pericàs.   

Abstract

A new tris(1-benzyl-1H-1,2,3-triazol-4-yl)methanol ligand 3 has been prepared by a triple Cu(I)-catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC). Ligand 3 forms a stable complex with CuCl, which catalyzes the Huisgen 1,3-dipolar cycloaddition on water or under neat conditions. Low catalyst loadings, short reaction times at room temperature, and compatibility with free amino groups make 3.CuCl an outstanding catalyst for CuAAC.

Entities:  

Year:  2009        PMID： 19775097     DOI： 10.1021/ol9018776

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Intracellular detection of cytosine incorporation in genomic DNA by using 5-ethynyl-2'-deoxycytidine.

Authors:  Lirui Guan; Godfried W van der Heijden; Alex Bortvin; Marc M Greenberg
Journal:  Chembiochem       Date:  2011-08-01       Impact factor: 3.164

2.  Cucurbit[7]uril Enables Multi-Stimuli-Responsive Release from the Self-Assembled Hydrophobic Phase of a Metal Organic Polyhedron.

Authors:  Soumen K Samanta; Jeffrey Quigley; Brittany Vinciguerra; Volker Briken; Lyle Isaacs
Journal:  J Am Chem Soc       Date:  2017-06-23       Impact factor: 15.419

3.  Tailored ligand acceleration of the Cu-catalyzed azide-alkyne cycloaddition reaction: practical and mechanistic implications.

Authors:  Stanislav I Presolski; Vu Hong; So-Hye Cho; M G Finn
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

4.  Continuous-flow enantioselective α-aminoxylation of aldehydes catalyzed by a polystyrene-immobilized hydroxyproline.

Authors:  Xacobe C Cambeiro; Rafael Martín-Rapún; Pedro O Miranda; Sonia Sayalero; Esther Alza; Patricia Llanes; Miquel A Pericàs
Journal:  Beilstein J Org Chem       Date:  2011-10-31       Impact factor: 2.883

Review 5.  Advancements in the mechanistic understanding of the copper-catalyzed azide-alkyne cycloaddition.

Authors:  Regina Berg; Bernd F Straub
Journal:  Beilstein J Org Chem       Date:  2013-12-02       Impact factor: 2.883

6.  Copper(I)-Phosphinite Complexes in Click Cycloadditions: Three-Component Reactions and Preparation of 5-Iodotriazoles.

Authors:  Juana M Pérez; Peter Crosbie; Steven Lal; Silvia Díez-González
Journal:  ChemCatChem       Date:  2016-06-13       Impact factor: 5.686

7.  A fully recyclable heterogenized Cu catalyst for the general carbene transfer reaction in batch and flow.

Authors:  Lourdes Maestre; Erhan Ozkal; Carles Ayats; Álvaro Beltrán; M Mar Díaz-Requejo; Pedro J Pérez; Miquel A Pericàs
Journal:  Chem Sci       Date:  2014-11-28       Impact factor: 9.825

Review 8.  Development and Applications of the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) as a Bioorthogonal Reaction.

Authors:  Li Li; Zhiyuan Zhang
Journal:  Molecules       Date:  2016-10-24       Impact factor: 4.411

Review 9.  Recent Progress of Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions (CuAAC) in Sustainable Solvents: Glycerol, Deep Eutectic Solvents, and Aqueous Media.

Authors:  Noel Nebra; Joaquín García-Álvarez
Journal:  Molecules       Date:  2020-04-26       Impact factor: 4.411

10.  Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production.

Authors:  Sándor B Otvös; Adám Georgiádes; István M Mándity; Lóránd Kiss; Ferenc Fülöp
Journal:  Beilstein J Org Chem       Date:  2013-07-29       Impact factor: 2.883
  10 in total

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