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Benchtop factory for cross-coupling reactions by circulatory catalyst flow using low-viscosity ionic liquid as reaction medium and catalyst support

Benchtop factory for cross-coupling reactions by circulatory catalyst flow using low-viscosity... Abstract This article describes the development of a circulatory catalyst flow system for Pd-catalyzed cross-coupling reactions, such as the Mizoroki-Heck reaction and the Sonogashira reaction, in which low-viscosity ionic liquids such as (bmim)NTf 2 and (emim)NTf 2 were used as a recyclable reaction medium and a catalyst support. A benchtop production system consisting of a flow reactor (micromixer plus residence time unit), a dual extraction unit with two T-shaped micromixers, and a catalyst/solvent pumping back system has been designed and tested for a 100 g scale synthesis using the Mizoroki-Heck reaction, which indeed worked well. Using a similar continuous-flow equipment, 103 g of the key intermediate of the matrix metalloproteinase inhibitor was synthesized by Cu-free Sonogashira reaction with (emim)NTf 2 as a solvent, in which the system was run for 5.5 h. The attributes of facile separation and recycling of both the catalyst and the ionic liquid reaction medium impart certain characteristics of heterogeneous catalysis to this continuous-flow system. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Green Processing and Synthesis de Gruyter

Benchtop factory for cross-coupling reactions by circulatory catalyst flow using low-viscosity ionic liquid as reaction medium and catalyst support

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Publisher
de Gruyter
Copyright
Copyright © 2012 by the
ISSN
2191-9542
eISSN
2191-9550
DOI
10.1515/gps-2011-0008
Publisher site
See Article on Publisher Site

Abstract

Abstract This article describes the development of a circulatory catalyst flow system for Pd-catalyzed cross-coupling reactions, such as the Mizoroki-Heck reaction and the Sonogashira reaction, in which low-viscosity ionic liquids such as (bmim)NTf 2 and (emim)NTf 2 were used as a recyclable reaction medium and a catalyst support. A benchtop production system consisting of a flow reactor (micromixer plus residence time unit), a dual extraction unit with two T-shaped micromixers, and a catalyst/solvent pumping back system has been designed and tested for a 100 g scale synthesis using the Mizoroki-Heck reaction, which indeed worked well. Using a similar continuous-flow equipment, 103 g of the key intermediate of the matrix metalloproteinase inhibitor was synthesized by Cu-free Sonogashira reaction with (emim)NTf 2 as a solvent, in which the system was run for 5.5 h. The attributes of facile separation and recycling of both the catalyst and the ionic liquid reaction medium impart certain characteristics of heterogeneous catalysis to this continuous-flow system.

Journal

Green Processing and Synthesisde Gruyter

Published: Oct 1, 2012

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