Rapid Reduction of Nitriles to Primary Amines With Nickel Boride at Ambient Temperature[1]

An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-D-glucopyranoside

“…Probably due to the adsorption of the resulted amine on the hydrogenation catalyst, the deiodinated nitrile 6d was the major product with a moderate yield (62%). In contrast, the conditions with NaBH 4 -NiCl 2 [10] in ethanol enabled both of the desired reactions as mentioned above. In the crude amine, however, three of the four acetyl protective groups were removed under basic conditions, as suggested by 1 H NMR.…”

Raney Ni/KBH4: An efficient and mild system for the reduction of nitriles to amines

“…2 Therefore, transforming nitriles to primary amines with high selectivity and yields has become an important field to chemists. 3,5,6,7,12,13 …”

NiCl2and NiCl2= 6H2O: A very Useful Mild Lewis Acid in Organic Synthesis

“…3 NiCl 2 is a selective reductive agent when used with hydrides such as LiAlH 4 and NaBH 4 . In fact, the mixture of NiCl 2 and NaBH 4 is used to prepare nickel boride, 4 a reducing agent for many functional groups: azide, 5 nitrile, 6 NO bond, 7 alkene 8 and haloalkane. 9 NiCl 2 was used in the regioselective rearrangement of dienols, 10 ring-opening of epoxide, 11 nickel(II)/chromium(II) chloride-mediated addition to aldehydes or ketones, 2,3 Suzuki cross-coupling, 12 Biginelli reaction, 13 reductive Heck-like reactions, 14 nickel-catalyzed cross-coupling reaction of Grignard reagents 15 and homo-coupling reactions.…”

“…18 (F) Nitriles are rapidly reduce to primary amines with nickel boride at room temperature. 6 (F) A Biginelli reaction was efficiently used for the synthesis of 3,4-dihydropyrimidinones from aldehydes, β-keto esters and urea in ethanol, using NiCl 2 ·6H 2 O. 13 (G) An intramolecular Nozaki-Kishi cyclization was efficiently employed in the cyclization of Z-vinyl bromides to the corresponding cyclopentenols in good yields.…”