Copper-catalysed ligation of azides and acetylenes
AssigneeThe Scripps Research Institute
InventorsK. Barry Sharpless, Valery Fokin, Vsevold V. Rostovtsev, Luke Green, Fahmi Himo
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Abstract
A copper catalyzed click chemistry ligation process is employed to bind azides and terminal acetylenes to provide 1,4-disubstituted 1,2,3-triazole triazoles. The process comprises contacting an organic azide and a terminal alkyne with a source of reactive Cu(I) ion for a time sufficient to form by cycloaddition a 1,4-disubstituted 1,2,3-triazole. The source of reactive Cu(I) ion can be, for example, a Cu(I) salt or copper metal. The process is preferably carried out in a solvent, such as an aqueous alcohol. Optionally, the process can be performed in a solvent that comprises a ligand for Cu(I) and an amine.
Claims32
A copper catalyzed process for preparing a 1,4-disubstituted 1,2,3-triazole comprising:
- contacting an organic azide and a terminal alkyne with a source of reactive Cu(I) ion for time sufficient to form by cycloaddition a 1,4-disubstituted 1,2,3-triazole, wherein said source of reactive Cu(I) ion comprises a Cu(I) salt, and wherein the organic azide, the terminal alkyne, and the Cu(I) salt are present in a solution comprising a ligand for Cu(I) and an amine.
A copper catalyzed process for preparing a 1,4-disubstituted 1,2,3-triazole comprising:
- contacting an organic azide and a terminal alkyne with a source of reactive Cu(I) ion for a time sufficient to form by cycloaddition a 1,4-disubstituted 1,2,3-triazole, wherein said source of reactive Cu(I) ion comprises a Cu(I) salt, and wherein the organic azide, the terminal alkyne, and the Cu(I) salt are present in a solution that is substantially free from oxygen.
A copper catalyzed process for preparing a 1,4-disubstituted 1,2,3-triazole comprising:
- contacting an organic azide and a terminal alkyne with copper metal for a time sufficient to form by cycloaddition a 1,4-disubstituted 1,2,3-triazole, wherein the organic azide and the terminal alkyne are present in a solvent.
A copper catalyzed process for preparing a 1,4-disubstituted 1,2,3-triazole comprising:
- contacting an organic azide and a terminal alkyne with a source of reactive Cu(I) ion for a time sufficient to form by cycloaddition a 1,4-disubstituted 1,2,3-triazole, wherein the source of reactive Cu(I) ion comprises a Cu(II) salt and a reducing agent for reducing Cu(II) to Cu(I).
A process for preparing a 1,4-disubstituted 1,2,3-triazole comprising:
- contacting a solution of organic azide and a terminal alkyne with a source of reactive Cu(I) ion comprising a Cu(II) salt, a reducing agent for Cu(II), and a ligand for copper, for a time sufficient to form by cycloaddition a 1,4-disubstituted 1,2,3-triazole.
A copper catalyzed process for preparing a 1,4-disubstituted 1,2,3-triazole comprising:
- contacting an organic azide and a terminal alkyne with a source of reactive Cu(I) ion for a time sufficient to form by cycloaddition a 1,4-disubstituted 1,2,3-triazole, wherein the source of reactive Cu(I) ion comprises a Cu(I) salt, and wherein the organic azide, the terminal alkyne, and the Cu(I) salt are in solution together with a reducing agent and a ligand for Cu(I).
Dependencies are inferred from the claim text.