Catalyst and battery components derived from condensation reactions with carba-closo-dodecaborate amines

US9994595B2 · kind B2 · utility

Assignee

• The Regents of the University of California · US

Inventors

• Vincent Lavallo · Oakland, US
• Ahmad El Hellani · Oakland, US
• Allen H. Chan · Hamilton, CA

Key dates

• Filing date: Mar 16, 2015
• Grant date: Jun 12, 2018
• Expiry date: Mar 16, 2035

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02E60/10
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Described herein is the fusion of two families of unique carbon-containing molecules that readily disregard the tendency of carbon to form four chemical bonds, namely N-heterocyclic carbenes (NHCs) and carborane anions. Deprotonation of an anionic imidazolium salt with lithium diisopropylamide at room temperature leads to a mixture of lithium complexes of C-2 and C-5 dianionic NHC constitutional isomers as well as a trianionic (C-2, C-5) adduct. Judicious choice of the base and reaction conditions allows for the selective formation of all three stable polyanionic carbenes. In solution, the so-called abnormal C-5 NHC lithium complex slowly isomerizes to the normal C-2 NHC, and the process can be proton catalyzed by the addition of the anionic imidazolium salt. These results indicate that the combination of two unusual forms of carbon atoms can lead to unexpected chemical behavior, and that this strategy paves the way for the development of a broad new generation of NHC ligands for catalysis.