Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions

• Lukas Kupracz,
• Jan Hartwig,
• Jens Wegner,
• Sascha Ceylan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2011, 7, 1441–1448, doi:10.3762/bjoc.7.168

• -type cycloadditions The copper-catalyzed Huisgen-type cycloaddition (CuAAC) is a general and useful method for the synthesis of 1,4-disubstituted-1,2,3-triazoles and is based on the 1,3-dipolar cycloaddition of alkynes and azides [28]. Besides Cu(I) sources also Cu(0) sources, such as copper wire [29

• ] or copper-on-charcoal (Cu/C) [30], can serve as a catalytic source that promotes the CuAAC. Bogdan et al. combined this observation with flow technology by using a custom-made heated copper flow reactor [31]. We successfully implemented the CuAAC by inductively heating copper wire inside a flow

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• –alkyne cycloaddition (CuAAC) reaction [33][34]. Results and Discussion Since their introduction by Palcic and co-workers [35], hydrophobic alkyl glycosides have proven to be valuable derivatives for enzymatic assays, as their lipophilic nature allows easy product isolation by either reversed-phase

New amphiphilic glycopolymers by click functionalization of random copolymers – application to the colloidal stabilisation of polymer nanoparticles and their interaction with concanavalin A lectin

• Otman Otman,
• Paul Boullanger,
• Eric Drockenmuller and
• Thierry Hamaide

Beilstein J. Org. Chem. 2010, 6, No. 58, doi:10.3762/bjoc.6.58

• cycloaddition of azide and alkynes, CuAAC) constitutes another interesting approach. The versatile nature of this reaction has led to a tremendous amount of work, mainly due to the quantitative yields and the possibility of carrying out the synthesis in either organic solvents or water. Moreover, since various

• ), 26.00–26.07 (C-6, C-8), 18.57 (C-3). Coupling of azido functionalized carbohydrates by CuAAC The dry copolymer (100 mg, containing approximately 75 mg, 0.68 mmol of propargyl acrylate) and compound 4 (229 mg, 1.0 equiv vs propargyl acrylate) were dissolved in a 1:1 mixture of THF and water (4 mL) at