Applications of catalysis in hydroboration of imines, nitriles, and carbodiimides

Abstract

The catalytic hydroboration of imines, nitriles, and carbodiimides is a powerful method of preparing amines which are key syn-thetic intermediates in the synthesis of many value-added products. Imine hydroboration has...

Reactions of nickel boranyl compounds with pnictogen–carbon triple bonds

“…2). However, no reaction was concluded between 1 and (1-Ad)CN by 31 P{ 1 H} NMR spectroscopy. Additional heating of the reaction mixture at 60 °C over 48 h likewise provided no evidence for (1-Ad)CN coordination or even decay of 1, suggesting that the 1-Ad group inhibits nitrile binding, which is contrasted with the facile coordination observed for CH 3 CN and PhCN.…”

“…2). Analysis by 31 P{ 1 H} NMR spectroscopy showed a new set of [AB]-doublets at d P = 67.3 and 70.4 ppm ( 2 J P,P = 45.7 Hz), suggesting consumption of 1 and formation of a new nitrile-bound C 1symmetric complex 2, isolated as a yellow solid in 76% yield (Fig. 2).…”

“…2). Analysis by 31 To investigate the effect of nitrile steric bulk on dimer formation, complex 1 was reacted with adamantyl nitrile (1-Ad) CN (Fig. 2).…”

Hydroboration of imines: intermolecularvs.intramolecular hydride transfer

“…1,2 Hydroboration, arguably, represents one of the most used synthetic approaches for this purpose and it involves the addition of a B-H bond across the unsaturated fragment. [3][4][5] The use of different boron-based reagents (HBpin, HBcat, Me 2 S-BH 3 , etc. ), solvent medium (including solvent-less reactions) and different species as catalysts/initiators has been extensively examined.…”

Tropylium tetrafluoroborate promoted hydroboration of nitriles, imines and amides

“…The latter strategy, often termed hydroboration of nitriles, is milder and more selective and has become the main focus of development in laboratories in recent years. 1 b ,2…”