Issue 2, 2023

In situ generated aminodiborane as a reagent for deoxygenative reduction of carboxamides to amines

Abstract

Herein, we report a new method for the synthesis of aminodiborane (μ-NH2B2H5) by the reaction of NH3BH3 and elemental iodine (I2). The in situ generated aminodiborane is used as a reagent for the reduction of carboxamides to amines. This method is applicable to obtain various secondary amides, tertiary amides, and trifluoroamides, with yields in the range of 67–94%. This protocol is also useful for preparing galipinine, cinacalcet and tetracaine hydrochloride, which are pharmaceutically important compounds. Control experiments and DFT studies have been carried out to explore the mechanistic pathway. These studies indicate that the active reagent in the reduction of secondary amides is aminodiborane and in the case of tertiary amides, aminodiborane and polyaminoborane.

Graphical abstract: In situ generated aminodiborane as a reagent for deoxygenative reduction of carboxamides to amines

Supplementary files

Article information

Article type
Research Article
Submitted
28 okt 2022
Accepted
01 dec 2022
First published
01 dec 2022

Org. Chem. Front., 2023,10, 327-334

In situ generated aminodiborane as a reagent for deoxygenative reduction of carboxamides to amines

A. Nair, V. Tiwari, A. Verma, P. Saini and A. J. Elias, Org. Chem. Front., 2023, 10, 327 DOI: 10.1039/D2QO01717B

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