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Issue 14, 2020
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Monoalkylation of aniline with trichloroacetimidate catalyzed by (±)-camphorsulfonic acid through an SN1 reaction based on dual hydrogen-bonding activation modes

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Abstract

Monoalkylation of aniline can be readily achieved using trichloroacetimidate as an alkylating agent and a Brønsted acid, such as (±)-camphorsulfonic acid, as a catalyst. In this study, systematic theoretical calculations were performed to understand the reaction mechanism for the monoalkylation of 2,5-dichloroaniline with trichloroacetimidate catalyzed by (±)-camphorsulfonic acid; moreover, the judgement about whether the reaction takes place via an SN1 or SN2 mechanism was elaborated. The two possible proton-transfer reaction mechanisms proposed herein based on the experimental results were investigated; moreover, another two possible reaction mechanisms involving the activation of both 2,5-dichloroaniline and trichloroacetimidate by (±)-camphorsulfonic acid via dual hydrogen-bonding activation modes were evaluated. The calculated results suggest that the reaction between 2,5-dichloroaniline and trichloroacetimidate catalyzed by (±)-camphorsulfonic acid preferentially occurs through the SN1 mechanism based on the dual hydrogen-bonding activation modes.

Graphical abstract: Monoalkylation of aniline with trichloroacetimidate catalyzed by (±)-camphorsulfonic acid through an SN1 reaction based on dual hydrogen-bonding activation modes

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Article information


Submitted
15 Jan 2020
Accepted
12 Mar 2020
First published
12 Mar 2020

New J. Chem., 2020,44, 5526-5534
Article type
Paper

Monoalkylation of aniline with trichloroacetimidate catalyzed by (±)-camphorsulfonic acid through an SN1 reaction based on dual hydrogen-bonding activation modes

K. Lu, Y. Dai, C. Yan, F. Yang, X. Yang, P. Zhou and Z. Yang, New J. Chem., 2020, 44, 5526
DOI: 10.1039/D0NJ00239A

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