Insight into the Amine-Assisted Metal-free Chemoselctive Reductive Amination of Carbonyl Compounds Under Mild Conditions

10 April 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Tertiary amines are ubiquitous and play an essential role in organocatalysis, pharmaceuticals, and fine chemicals. Amongst various synthetic procedures known for their synthesis, the reductive amination of carbonyl compounds has been found to be a proficient method. Over the past few decades, different synthetic strategies for reductive amination have been developed. Most of them suffer from the use of transition metals and/or harsh reaction conditions. Herein, we present an efficient, operationally simple protocol for the chemoselective reductive amination of carbonyl compounds to furnish the tertiary amines. The strategy encompasses broad substrate scope under the metal-free condition at room temperature and does not require any solvent. A detailed mechanistic investigation was executed with the aid of control experiments and computational study to shed light on the reaction pathway.

Keywords

Metal-free
Amination

Supplementary materials

Title
Description
Actions
Title
Insight into the Amine-Assisted Metal-free Chemoselctive Reductive Amination of Carbonyl Compounds Under Mild Conditions
Description
Herein, we report an operationally simple procedure for synthesizing alkylated tertiary amines starting from the aldehydes and dimethylamine borane (DMAB) under metal-free conditions. Remarkably, this protocol does not require any external amine substrate and proceeds with transferring the dimethylamine group from DMAB. The reaction proceeds at room temperature within 30 minutes under neat conditions. The current strategy encompasses a broad substrate scope, and aldehydes and ketones having various functional groups undergo the reaction to furnish the corresponding tertiary amines chemoselectively. Further, control experiments and detailed computational studies were performed to gain insight into the reaction mechanism.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.