Issue 110, 2016, Issue in Progress
From the journal:

RSC Advances

Catalyst free decarboxylative trichloromethylation of aldimines†

Eloah P. Ávila,a   Isabella F. de Souza,a   Alline V. B. Oliveira,b   Vinicius Kartnaller,b   João Cajaiba,b   Rodrigo O. M. A. de Souza,b   Charlane C. Corrêaa  and  Giovanni W. Amarante*a  

* Corresponding authors

a Departamento de Química, Universidade Federal de Juiz de Fora, Juiz de Fora, MG, Brazil
E-mail: giovanni.amarante@ufjf.edu.br

b Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, Brazil

Abstract

A catalyst free decarboxylative trichloromethylation of imines to afford different trichloromethyl sulfonyl and sulfinyl amines has been presented. Only DMSO as a solvent at room temperature was necessary to provide the corresponding products in good to high isolated yields. A highly diastereoselective version was carried out, leading to the sulfinylimine with good yield and near perfect diastereoselectivity. Regarding the reaction profile, ATR-FTIR spectroscopy was employed to support the entire mechanism and also to provide details on the trichloroacetate salts behavior against electrophiles and in the presence of different solvents.

Graphical abstract: Catalyst free decarboxylative trichloromethylation of aldimines

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Article information

DOI
https://doi.org/10.1039/C6RA23936F
Article type
Communication
Submitted
26 Sep 2016
Accepted
08 Nov 2016
First published
09 Nov 2016

RSC Adv., 2016,6, 108530-108537

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Catalyst free decarboxylative trichloromethylation of aldimines

E. P. Ávila, I. F. de Souza, A. V. B. Oliveira, V. Kartnaller, J. Cajaiba, R. O. M. A. de Souza, C. C. Corrêa and G. W. Amarante, RSC Adv., 2016, 6, 108530 DOI: 10.1039/C6RA23936F

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