Copper-catalysed ligation of azides and acetylenes

US8580970B2 · kind B2 · utility

Assignee

• THE SCRIPPS RESEARCH INSTITUTE · US

Inventors

• K. Barry Sharpless · Brookline, US
• Valery Fokin · Oceanside, US
• Vsevold V. Rostovtsev · Wilmington, US
• Luke Green · Basel, CH
• Fahmi Himo · Solna, SE

Key dates

• Filing date: Mar 5, 2012
• Grant date: Nov 12, 2013
• Expiry date: Mar 5, 2032

Classification

• Technology area (CPC B): Performing Operations; Transporting
• CPC primary: B01J2531/96
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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.