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Alkali Metal–Promoted Facile Synthesis of Secondary Amines from Imines and Carbodiimides
, I. Banerjee, S. Sagar
Published in John Wiley and Sons Ltd
2020
Volume: 34
   
Issue: 9
Abstract
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. © 2020 John Wiley & Sons, Ltd.
About the journal
JournalData powered by TypesetApplied Organometallic Chemistry
PublisherData powered by TypesetJohn Wiley and Sons Ltd
ISSN02682605