Acid-base jointly promoted copper(I)-catalyzed azide-alkyne cycloaddition.

In this novel acid-base jointly promoted CuAAC, the combination of CuI/DIPEA/HOAc was developed as a highly efficient catalytic system. The functions of DIPEA and HOAc have been assigned, and HOAc was recognized to accelerate the conversions of the C-Cu bond-containing intermediates and buffer the basicity of DIPEA. As a result, all drawbacks occurring in the popular catalytic system CuI/NR(3) were overcome easily.

[1]  Yuefei Hu,et al.  Carboxylic acid-promoted copper(I)-catalyzed azide-alkyne cycloaddition. , 2010, The Journal of organic chemistry.

[2]  U. Nilsson,et al.  C2-symmetric macrocyclic carbohydrate/amino acid hybrids through copper(I)-catalyzed formation of 1,2,3-triazoles. , 2005, The Journal of organic chemistry.

[3]  M. Yus,et al.  Unsupported copper nanoparticles in the 1,3-dipolar cycloaddition of terminal alkynes and azides , 2010 .

[4]  Chi‐Huey Wong,et al.  Synthesis of sugar arrays in microtiter plate. , 2002, Journal of the American Chemical Society.

[5]  Efficient route to C2 symmetric heterocyclic backbone modified cyclic peptides. , 2005, Organic letters.

[6]  Ben L Feringa,et al.  Phosphoramidite accelerated copper(i)-catalyzed [3 + 2] cycloadditions of azides and alkynes. , 2009, Chemical communications.

[7]  Vijayendra S. Shetti,et al.  Synthesis of Triazole‐Bridged Unsymmetrical Porphyrin Dyads and Porphyrin–Ferrocene Conjugates , 2010 .

[8]  H. Hiemstra,et al.  CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective , 2005 .

[9]  Jason E Hein,et al.  Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides. , 2010, Chemical Society reviews.

[10]  M Reza Ghadiri,et al.  A heterocyclic peptide nanotube. , 2003, Journal of the American Chemical Society.

[11]  A. Marra,et al.  C-glycoside clustering on calix[4]arene, adamantane, and benzene scaffolds through 1,2,3-triazole linkers. , 2006, The Journal of organic chemistry.

[12]  K. Kirshenbaum,et al.  Peptide cyclization and cyclodimerization by Cu(I)-mediated azide-alkyne cycloaddition. , 2009, The Journal of organic chemistry.

[13]  Stuart L Schreiber,et al.  Synthesis and cellular profiling of diverse organosilicon small molecules. , 2007, Journal of the American Chemical Society.

[14]  Hai Yu,et al.  Chemoenzymatic synthesis of size-defined polysaccharides by sialyltransferase-catalyzed block transfer of oligosaccharides. , 2007, Journal of the American Chemical Society.

[15]  J. Herscovici,et al.  Automated Synthesis of a 96 Product-Sized Library of Triazole Derivatives Using a Solid Phase Supported Copper Catalyst , 2010, Molecules.

[16]  Nicholas W. Smith,et al.  Base and concentration effects on the product distribution in copper-promoted alkyne–azide cycloaddition: additive-free route to 5-iodo-triazoles , 2010 .

[17]  Sachiko Sato,et al.  Carbohydrate triazoles and isoxazoles as inhibitors of galectins-1 and -3. , 2006, Chemical communications.

[18]  K. Kirshenbaum,et al.  Click to fit: versatile polyvalent display on a peptidomimetic scaffold. , 2005, Organic letters.

[19]  S. Chandrasekaran,et al.  Click chemistry inspired synthesis of ferrocene amino acids and other derivatives , 2010 .

[20]  S. Luo,et al.  Evolution of pyrrolidine-type asymmetric organocatalysts by "click" chemistry. , 2006, The Journal of organic chemistry.

[21]  P. Gmeiner,et al.  Click linker: efficient and high-yielding synthesis of a new family of SPOS resins by 1,3-dipolar cycloaddition. , 2003, Organic letters.

[22]  J. Porco,et al.  Synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by copper-catalyzed cycloaddition-coupling of azides and terminal alkynes , 2006 .

[23]  C. Jimeno,et al.  Polystyrene-supported hydroxyproline: an insoluble, recyclable organocatalyst for the asymmetric aldol reaction in water. , 2006, Organic letters.

[24]  A. Caminade,et al.  Synthesis and application of phosphorus dendrimer immobilized azabis(oxazolines). , 2007, Organic letters.

[25]  Peter Mayer,et al.  Isolation of a copper(I) triazolide: a "click" intermediate. , 2007, Angewandte Chemie.

[26]  K. Kirshenbaum,et al.  Tricks with clicks: modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition. , 2010, Chemical Society reviews.

[27]  Morten Meldal,et al.  Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. , 2002, The Journal of organic chemistry.

[28]  M. Finn,et al.  In situ click chemistry: probing the binding landscapes of biological molecules. , 2010, Chemical Society reviews.

[29]  T. Kirchhausen,et al.  Synthesis of a 10,000-membered library of molecules resembling carpanone and discovery of vesicular traffic inhibitors. , 2006, Journal of the American Chemical Society.

[30]  Steven V Ley,et al.  [3 + 2] Cycloaddition of acetylenes with azides to give 1,4-disubstituted 1,2,3-triazoles in a modular flow reactor. , 2007, Organic & biomolecular chemistry.

[31]  D. Gin,et al.  Highly convergent synthesis of C3- or C2-symmetric carbohydrate macrocycles. , 2005, Organic letters.

[32]  Fr. Moulin Recherches sur les benzyl‐l‐ et phényl‐1‐triazoles‐1,2,3 substitués , 1952 .

[33]  Luke G Green,et al.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. , 2002, Angewandte Chemie.

[34]  Morten Meldal,et al.  Cu-catalyzed azide-alkyne cycloaddition. , 2008, Chemical reviews.

[35]  B. Tekwani,et al.  Non-peptide macrocyclic histone deacetylase inhibitors derived from tricyclic ketolide skeleton. , 2010, Journal of medicinal chemistry.

[36]  B. Sreedhar,et al.  Regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles via three-component coupling of secondary alcohols, TMSN3 and alkynes , 2007 .

[37]  C. Seto,et al.  A two stage click-based library of protein tyrosine phosphatase inhibitors. , 2007, Bioorganic & medicinal chemistry.

[38]  D. Gin,et al.  Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide. , 2004, Journal of the American Chemical Society.

[39]  S. Schreiber,et al.  Macrocycloadditions leading to conformationally restricted small molecules. , 2006, Organic letters.

[40]  N. Sewald,et al.  "Clicktophycin-52": a bioactive cryptophycin-52 triazole analogue. , 2010, Organic letters.

[41]  A. Flood,et al.  Click chemistry generates privileged CH hydrogen-bonding triazoles: the latest addition to anion supramolecular chemistry. , 2010, Chemical Society reviews.

[42]  Q. Wang,et al.  Fluorogenic click reaction. , 2010, Chemical Society reviews.

[43]  H. Sharghi,et al.  Copper Nanoparticles on Charcoal for Multicomponent Catalytic Synthesis of 1,2,3‐Triazole Derivatives from Benzyl Halides or Alkyl Halides, Terminal Alkynes and Sodium Azide in Water as a “Green” Solvent , 2009 .

[44]  Kevin D. Haenni,et al.  The application of CuAAC 'click' chemistry to catenane and rotaxane synthesis. , 2010, Chemical Society reviews.

[45]  G. Tron,et al.  One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloaddition. , 2006, Organic letters.

[46]  Yuefei Hu,et al.  Copper(I) Acetate: A Structurally Simple but Highly Efficient Dinuclear Catalyst for Copper‐Catalyzed Azide‐Alkyne Cycloaddition , 2010 .

[47]  Ibrahim Jibril,et al.  Dipolar cycloaddition reactions of organic azides with some acetylenic compounds , 1989 .