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Catalytic Hydroboration of Organic Nitriles Promoted by Aluminum Complex
Author(s) -
Harinath Adimulam,
Bhattacharjee Jayeeta,
Panda Tarun K.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801252
Subject(s) - hydroboration , chemistry , catalysis , toluene , yield (engineering) , alkyl , hydride , organic synthesis , organic chemistry , solvent , medicinal chemistry , hydrogen , materials science , metallurgy
We demonstrate an efficient protocol for the chemoselective hydroboration of organic nitriles with pinacolborane (HBpin) and catecholborane (HBcat) using aluminum alkyl complex [ κ 2 ‐{2‐F−C 6 H 4 NP(Se)Ph 2 } 2 Al−(Me)] as a pre‐catalyst to afford diboryl amines under solvent‐free and mild conditions (60 °C) in high yield. The aluminum complex was prepared by the reaction of [2‐F−C 6 H 4 NHP(Se)Ph 2 ] and trimethylaluminum in toluene. The solid‐state structure of Al complex is established. Nitriles with a wide array of electron‐withdrawing and electron‐donating functional groups were easily converted to the desired products through the formation of aluminum hydride as an active species. A kinetic study of the catalytic reaction is also reported.