Addition of boranes to N-aryl-salicylaldimines: Intramolecular hydrogenation of imines

Abstract

Addition of boranes to N-aryl-salicylaldimines takes place initially at the reactive phenolic O-H bond to give an activated boron-containing imine and dihydrogen. In some cases a subsequent intramolecular hydrogenation step is observed and the C=N imine bond is reduced to the corresponding amine. Reactions with dimesitylborane in THF are unique in that the reduced amine product is the major product observed in solution.

Chemistry on Boranils: An Entry to Functionalized Fluorescent Dyes

“…Starting from the fluorescent Boranil compound A , we investigated its conversion into more useful derivatives. In contrast to known procedures where Boranil compounds were reduced in situ by borane to the corresponding amino-phenol borate, we were pleased to find that, with soft hydrogenation, we could obtain almost quantitatively the amino derivative 1 (Scheme ) without reducing the imino fragment. This key synthon 1 was obtained by a standard reduction of the nitro parent under H 2 catalyzed by palladium on carbon at rt.…”

Oxidative coupling of silylated nonagermanide clusters

“…Inspection of the light-yellow crystals revealed the lattice parameters previously obtained for Cy 2 B-O-BCy 2 isolated from the reaction of Cy 2 BH and H 2 O. 48 Furthermore, the observed 11 B NMR shift matches with the shift of the closely related boryl ether Me 2 B-O-BMe 2 (52 ppm). 49 Additionally, the mass peak of the ionization product [Cy 2 B-O-BCy] + was detected in LIFDI-MS measurements (Fig.…”

Oxygen insertion into boroles as a route to 1,2-oxaborines

“…1.351 (7)] which indicates delocalization of the p-electrons between the boron and oxygen. 58,59 It is also noteworthy that the endocyclic B-C bond [1.527(2)] is slightly shorter than the exocyclic bond [1.568(2)].…”