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Issue 2, 2020
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In water alkylation of amines with alcohols through a borrowing hydrogen process catalysed by ruthenium nanoparticles

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Abstract

A simple and environmentally benign procedure for the synthesis of secondary amines in water has been developed. Combining Ru3(CO)12, tetraphenylcyclopentadienone and a small quantity of TGPS-750-M surfactant, primary and secondary alcohols were alkylated at N employing equimolar amounts of aromatic amines in water. The reaction occurs under microwave (MW) dielectric heating with high conversion and high yield. When required, the use of biomass-derived 2-MeTHF or GVL as a co-solvent is possible. Under the influence of MWs, a Ru nanoparticle–nanomicelle combination was formed acting as an effective and recyclable catalyst. This protocol was also employed for “in water” cyclisation to synthesise biologically relevant pyrrolobenzodiazepines (PBDs).

Graphical abstract: In water alkylation of amines with alcohols through a borrowing hydrogen process catalysed by ruthenium nanoparticles

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Article information


Submitted
25 Sep 2019
Accepted
07 Dec 2019
First published
10 Dec 2019

Green Chem., 2020,22, 327-331
Article type
Communication

In water alkylation of amines with alcohols through a borrowing hydrogen process catalysed by ruthenium nanoparticles

C. Risi, M. Calamante, E. Cini, V. Faltoni, E. Petricci, F. Rosati and M. Taddei, Green Chem., 2020, 22, 327
DOI: 10.1039/C9GC03351C

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