Issue 40, 2012
From the journal:

Organic & Biomolecular Chemistry

Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity†

Azarmidokht Gholamipour-Shirazia  and  Christian Rolando*a  

* Corresponding authors

a USR CNRS 3290, Miniaturisation pour la Synthèse, l'Analyse et la Protéomique and FR CNRS 2638 Michel-Eugène Chevreul, Université de Lille 1, Sciences et Technologies, 59655 Villeneuve d'Ascq, France
E-mail: christian.rolando@univ-lille1.fr
Fax: +33 (0)3 20 33 61 36
Tel: +33 (0)3 20 43 49 77

Abstract

We describe here the determination of the alkylation rate of a set of organic superbases by iodomethane in DMF using a microfluidic continuous flow reactor. Surprisingly, log kAlkylation follows the inverse trend of pKBH+ of the base. Mayr's equation allows a more quantitative approach. From a synthetic point of view, TMGN and BEMP are demonstrated to be the best choices.

Graphical abstract: Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity

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Article information

DOI
https://doi.org/10.1039/C2OB25215E
Article type
Communication
Submitted
30 Jan 2012
Accepted
29 Aug 2012
First published
31 Aug 2012

Org. Biomol. Chem., 2012,10, 8059-8063

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Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity

A. Gholamipour-Shirazi and C. Rolando, Org. Biomol. Chem., 2012, 10, 8059 DOI: 10.1039/C2OB25215E

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