Related Experiment Video
Updated: Sep 27, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Hydroboration of nitriles and imines by highly active zinc dihydride catalysts
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University Suzhou 215123 P. R. China xinxu@suda.edu.cn.
Abstract:
Eco-friendly zinc dihydrides stabilized by N-heterocyclic carbenes were demonstrated to be highly efficient catalysts for the double hydroboration of nitriles with pinacolborane, exhibiting turnover frequencies up to 3000 h-1 at room temperature under solvent-free conditions. The reactions afforded corresponding diboronated amines with excellent yields and good functional group tolerance. A single Zn-H insertion product was isolated from a stoichiometric reaction of zinc dihydride with nitrile, and was proved to be an active species in this transformation. Kinetic studies were performed to give some insights into the catalytic reactions. In addition, zinc dihydride species also showed high activity for the hydroboration of imines to boronated amines.
More Related Videos
Related Concept Videos
Preparation of Nitriles
Nitriles to Amines: LiAlH4 Reduction
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Preparation of Amines: Reduction of Amides and Nitriles
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

