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Alkali Metal–Promoted Facile Synthesis of Secondary Amines from Imines and Carbodiimides
Author(s) -
Panda Tarun K.,
Banerjee Indrani,
Sagar Shweta
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5765
Subject(s) - chemistry , hydroboration , aldimine , catalysis , yield (engineering) , alkali metal , organic chemistry , hydride , hydrolysis , solvent , metal , combinatorial chemistry , materials science , metallurgy
We present here an efficient method for the hydroboration of aldimines (‐C=N‐) with pinacolborane (HBpin) using an alkali metal catalyst, potassium benzyl. The reaction was accomplished with unprecedented catalytic efficiency under mild and solvent‐free conditions to afford the high yield of the corresponding N‐boryl amines up to 97%. Various functionalities on aldimines were incorporated for hydroboration. The corresponding boryl amines were subjected to further hydrolysis to yield the corresponding secondary amines with good yields up to 89%. This protocol for the reaction demonstrates an atom‐economic and green method with diverse imines that bears excellent functional group tolerance. Chemoselective reduction of imines was also attained, with good yields of 74–89%. We also propose the most plausible mechanism involving the formation of metal hydride as the active pre‐catalyst.