Mailig, Melrose published the artcilePractical catalytic method for synthesis of sterically hindered anilines, Quality Control of 214360-44-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2015), 51(55), 11048-11051, database is CAplus and MEDLINE.
A practical catalytic method for the synthesis of sterically hindered anilines is described. The amination of aryl and heteroaryl boronic esters is accomplished using a catalyst prepared in situ from com. available and air-stable copper(I) triflate and a diphosphine ligand. For the first time, the method can be applied to the synthesis of both secondary and tertiary anilines in the presence of a wide range of functional groups. Esters, aldehydes, alcs., aryl halides, ketones, nitriles and nitro arenes are all compatible with the reaction conditions. Finally, even the most sterically hindered anilines can be successfully prepared under mild reaction conditions. Overall, the new method addresses significant practical limitations of a transformation previously developed and provides a valuable complement to the existing methods for the synthesis of anilines. Under optimized conditions the synthesis of the target compounds was achieved using 1,1′-(oxydi-2,1-phenylene)bis[1,1-dicyclohexylphosphine] (i.e. phosphine-ether) and copper(I) triflate compound with benzene (2:1) as ligand-catalyst combination. Starting materials included N-(benzoyloxy)-N-(1-methylethyl)-2-propanamine (hydroxylamine derivative), benzoic acid 1-pyrrolidinyl ester, 4-(benzoyloxy)-1-piperazinecarboxylic acid 1,1-dimethylethyl ester, benzoic acid 4-morpholinyl ester, benzoic acid 4-hydroxy-1-piperidinyl ester, benzoic acid 2,2,6,6-tetramethyl-1-piperidinyl ester. Boronic acid cyclic esters included 5,5-dimethyl-2-(2-methylphenyl)-1,3,2-dioxaborinane, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoic acid ester, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde, 2-chloro-3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine, 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyrimidine, 5,5-dimethyl-2-(3-thienyl)-1,3,2-dioxaborinane (thiophene derivative). The title compounds thus formed included 4-bromo-N,N-bis(1-methylethyl)benzenamine (tertiary amine, tertiary aniline), 2,6-dimethyl-N-(1-methylethyl)benzenamine (secondary amine, secondary aniline). The reaction of a [1,1′-(oxydi-2,1-phenylene)bis[1,1-dicyclohexylphosphine-.kappa .P]]copper complex intermediate with N-(benzoyloxy)-2-methyl-2-propanamine was reported.
Chemical Communications (Cambridge, United Kingdom) published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Quality Control of 214360-44-8.
Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts