One‐Pot Reductive Amination of Aromatic Aldehydes in [Et 3 NH][HSO 4 ] using Sodium Borohydride and A Mechanistic Investigation using Computational Method

Narvariya, Rajrani and Gupta, Shivangi and Panda, Tarun K and et al, . (2022) One‐Pot Reductive Amination of Aromatic Aldehydes in [Et 3 NH][HSO 4 ] using Sodium Borohydride and A Mechanistic Investigation using Computational Method. ChemistrySelect, 7 (4). ISSN 2365-6549

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Abstract

The reductive amination of aromatic aldehydes and aromatic amines, performed in the Brønsted acidic ionic liquid [Et3NH][HSO4], using sodium borohydride as a reducing agent is reported. In this protocol, the ionic liquid plays a crucial role in efficiently converting aromatic aldehydes to amines in excellent yields, without the formation of side products. In the presence of [Et3NH][HSO4], the imine was generated in situ from the reaction between the aromatic aldehydes and aromatic amines and underwent smooth reduction with sodium borohydride. This one-pot synthesis is practically simple and sustainable. The catalyst [Et3NH][HSO4] also has demonstrably wide applicability, in that it can be used with a variety of aromatic aldehydes and aromatic amines substituted by various electron-withdrawing and electron-donating groups. The role of IL [Et3NH][HSO4] in catalytic reductive amination is validated with the help of density functional theory (DFT)-based computational studies. © 2022 Wiley-VCH GmbH

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IITH Creators:

IITH Creators	ORCiD
Panda, Tarun K	http://orcid.org/0000-0003-0975-0118

Item Type:

Article

Additional Information:

This work was supported by Indian Institute of Technology Hyderabad. RN and PR thank CSIR, India for their PhD fellowships (09/1001(0040)2018-EMR-I) and (09/143(1001)-/2019-EMR-I) respectively. SG thanks UGC (NTA Ref. No. 191620057296) for her PhD fellowship. AJ acknowledges SERB-DST, India for TARE research fellowship (TAR/2020/000003). PG acknowledges SERB (CRG/2021/000759) for financial support and computational facilities by IIT Roorkee.

Uncontrolled Keywords:

aromatic aldehydes and aromatic amines, Brønsted acidic ionic liquid [Et3NH][HSO4], efficiently converting aromatic aldehydes to amines, role of IL [Et3NH][HSO4] in catalytic reductive amination.

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

14 Jul 2022 11:14

Last Modified:

14 Jul 2022 11:14

URI:

http://raiithold.iith.ac.in/id/eprint/9700