Organozinc complexes and processes for making and using the same

US9273070B2 · kind B2 · utility

Inventors

• Paul Knochel · Marburg, DE
• Sebastian Bernhardt · Munich, DE
• Georg Manolikakes · Frankfurt am Main, DE

Key dates

• Filing date: Dec 21, 2011
• Grant date: Mar 1, 2016
• Expiry date: Jul 23, 2032

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F7/1892
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Processes for making an organozinc reagents are disclosed comprising reacting (A) organomagnesium or organozinc complexes with (B) at least one coordination compound comprising one or more carboxylate groups and/or alcoholate groups and/or tertiary amine groups, optionally in combination with zinc ions and/or lithium ions and/or halide ions, wherein the halide ions are selected from chloride, bromide and iodide, the organozinc complex comprises an aryl group, a heteroaryl group or a benzyl group when the coordinating compound is a chelating polyamine, and the reaction is conducted in the presence of zinc complexed with at least one coordinating compound when reactant (A) comprises at least one organomagnesium complex. The resulting organozinc reagents may optionally be isolated from solvents to obtain a solid reagent. The reagents may be used for making organic compounds via Negishi cross-coupling reactions or via aldehyde and/or ketone oxidative addition reactions. The organozinc reagents are stable and, due to their high selectivity, permit maintenance of sensitive functional groups such as aldehydes during cross-coupling.