Alkali Metal–Promoted Facile Synthesis of Secondary Amines from Imines and Carbodiimides

Panda, Tarun K. and Banerjee, Indrani and Sagar, Shweta (2020) Alkali Metal–Promoted Facile Synthesis of Secondary Amines from Imines and Carbodiimides. Applied Organometallic Chemistry, 34 (9). ISSN 0268-2605

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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.

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IITH Creators:

IITH Creators	ORCiD
Panda, Tarun K	http://orcid.org/0000-0003-0975-0118
Banerjee, Indrani	UNSPECIFIED
Sagar, Shweta	UNSPECIFIED

Item Type:

Article

Uncontrolled Keywords:

Aldimines and carbodiimides; alkali metal alkyl; Chemoselectivity; hydroboration; Catalytic efficiencies; Chemoselective reduction; Facile synthesis; Metal catalyst; Metal hydrides; Plausible mechanisms; Secondary amines; Solvent free conditions

Subjects:

Chemistry
Chemistry > Techniques, procedures, apparatus, equipment, materials
Chemistry > Inorganic chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

15 Jun 2021 05:34

Last Modified:

15 Jun 2021 05:34

URI:

http://raiithold.iith.ac.in/id/eprint/7912