Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

Abstract

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid–base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

General Construction of Amine via Reduction of N=X (X = C, O, H) Bonds Mediated by Supported Nickel Boride Nanoclusters

“…Among these methods, the reduction of N= X ( X = C, O, H) bonds plays a key role. Generally, nitriles, nitro compounds and amides can be reduced to primary amines using borane [ 21 , 23 , 24 ], silane [ 25 ], hydrides [ 26 ], formats [ 20 , 27 ], alcohols [ 28 ], or molecular hydrogen [ 29 ]. Since Raney Ni was first prepared in 1905, it has become one of the most important catalysts for reduction.…”

Metal-Free Synthesis of 2-Substituted Quinazolines via Green Oxidation of o-Aminobenzylamines: Practical Construction of N-Containing Heterocycles Based on a Salicylic Acid-Catalyzed Oxidation System

“…All solvents were distilled before use. Compound 1b was prepared according to the previously reported procedure ( Amberchan et al, 2021 ). 1 H NMR spectra were recorded in CDCl 3 using the JEOL JNM-ECX400 (400 MHz) FT NMR, JEOL JNM-ECS400 (400 MHz) FT NMR, and the Bruker BioSpin Ascend 400 spectrometer (400 MHz) with Me 4 Si as the internal standard.…”

Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides

“…The following supporting information can be downloaded at: , the corresponding Cartesian coordinates in DFT studies, copies of NMR spectra for all new compounds, and a reference list for the characterization data of all known compounds [ 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 ].…”