A Boron-Nitrogen Double Transborylation Strategy for Borane-Catalyzed Hydroboration of Nitriles was written by Pradhan, Subham;Sankar, Raman Vijaya;Gunanathan, Chidambaram. And the article was included in Journal of Organic Chemistry in 2022.Reference of 4435-14-7 This article mentions the following:
Organoborane-catalyzed hydroboration of nitriles provides N,N-diborylamines, which act as efficient synthons for the synthesis of primary amines and secondary amides. Known nitrile hydroboration methods are dominated by metal catalysis. Simple and metal-free hydroboration of nitriles using diborane [H-B-9-BBN]2 as a catalyst and pinacolborane as a turnover reagent is reported. The reaction of monomeric H-B-9-BBN with nitriles leads to the hydrido-bridged diborylimine intermediate; a subsequent sequential double hydroboration-transborylation pathway involving B-N/B-H σ bond metathesis is proposed. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Reference of 4435-14-7).
2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Reference of 4435-14-7
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts