Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 7, 2020
Previous Article Next Article

Lithium amide catalyzed hydroboration of nitriles

Author affiliations

Abstract

The sequential combination of the facile substitution of organohalides with the nitrile function and the hydroboration of the resultant nitriles enables a straight-forward access to synthetically versatile primary amines via a formal C1 homologation. Several catalysts have been reported for the latter transformation, mostly with transition metal catalysts (Ti, Fe, Co, Ni, Zn, Ru, Mo). Very few main group metal catalysts have been demonstrated to show equal activity. This work reports an operationally facile hydroboration of nitriles at room temperature that operates under catalysis of the solid, stable, and inexpensive salt lithium hexamethyldisilazide, LiN(SiMe3)2. The reaction displayed good tolerance of functional groups including F, Cl, Br, I, pyridyl, and thiophene substituents. Carbonyl derivatives readily reacted under the same conditions. Mechanistic studies were indicative of the catalytic role of lithium amidinate intermediates, the co-catalytic role of nitrile additives, and a reaction order of zero in borane.

Graphical abstract: Lithium amide catalyzed hydroboration of nitriles

Back to tab navigation

Supplementary files

Article information


Submitted
19 Dec 2019
Accepted
28 Feb 2020
First published
03 Mar 2020

Org. Chem. Front., 2020,7, 960-966
Article type
Research Article

Lithium amide catalyzed hydroboration of nitriles

P. Ghosh and A. Jacobi von Wangelin, Org. Chem. Front., 2020, 7, 960
DOI: 10.1039/C9QO01507H

Social activity

Search articles by author

Spotlight

Advertisements