Copper-catalysed ligation of azides and acetylenes

US9302997B2 · kind B2 · utility

Assignee

• THE SCRIPPS RESEARCH INSTITUTE · US

Inventors

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

Key dates

• Filing date: May 6, 2015
• Grant date: Apr 5, 2016
• Expiry date: May 6, 2035

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 a solution of an organic azide and a terminal alkyne with a source of catalytic Cu(I) ion to form a 1,4-disubstituted 1,2,3-triazole, wherein the source of Cu(I) ion comprises Cu(II) and a metal capable of reducing Cu(II) to Cu(I). In some embodiments, the metal capable of reducing Cu(II) to Cu(I) is selected from the group consisting of Al, Be, Co, Cr, Fe, Mg, Mn, Ni, and Zn.