Literature DB >> 16586523

Microwave-assisted Suzuki coupling reactions with an encapsulated palladium catalyst for batch and continuous-flow transformations.

Ian R Baxendale1, Charlotte M Griffiths-Jones, Steven V Ley, Geoffrey K Tranmer.   

Abstract

This article describes the design, optimisation and development of a Suzuki cross-coupling protocol mediated by an efficient palladium-encapsulated catalyst (Pd EnCat) under microwave irradiation. The methodology has been used in both batch mode for classical library preparation and in continuous-flow applications furnishing multigram quantities of material. Described is a method that uses direct focused microwave heating whilst applying an external cooling source. This enables a lower than normal bulk temperature to be maintained throughout the reaction period leading to significant improvements in the overall yield and purity of the reaction products. Additional aspects of this novel heating protocol are discussed in relation to the prolonged lifetime and enhanced reactivity of the immobilised catalyst system.

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Year:  2006        PMID: 16586523     DOI: 10.1002/chem.200501400

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  16 in total

1.  The flow synthesis of heterocycles for natural product and medicinal chemistry applications.

Authors:  Marcus Baumann; Ian R Baxendale; Steven V Ley
Journal:  Mol Divers       Date:  2010-10-20       Impact factor: 2.943

Review 2.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

3.  Development of an automated microfluidic reaction platform for multidimensional screening: reaction discovery employing bicyclo[3.2.1]octanoid scaffolds.

Authors:  John R Goodell; Jonathan P McMullen; Nikolay Zaborenko; Jason R Maloney; Chuan-Xing Ho; Klavs F Jensen; John A Porco; Aaron B Beeler
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

4.  In situ generation and intramolecular Schmidt reaction of keto azides in a microwave-assisted flow format.

Authors:  Thomas O Painter; Paul D Thornton; Mario Orestano; Conrad Santini; Michael G Organ; Jeffrey Aubé
Journal:  Chemistry       Date:  2011-07-27       Impact factor: 5.236

5.  Polyionic polymers--heterogeneous media for metal nanoparticles as catalyst in Suzuki-Miyaura and Heck-Mizoroki reactions under flow conditions.

Authors:  Klaas Mennecke; Andreas Kirschning
Journal:  Beilstein J Org Chem       Date:  2009-05-08       Impact factor: 2.883

6.  Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Belgin Canturk; Lauren E Kennedy
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

7.  Rapid and efficient trifluoromethylation of aromatic and heteroaromatic compounds using potassium trifluoroacetate enabled by a flow system.

Authors:  Mao Chen; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-05       Impact factor: 15.336

8.  Replacing conventional carbon nucleophiles with electrophiles: nickel-catalyzed reductive alkylation of aryl bromides and chlorides.

Authors:  Daniel A Everson; Brittany A Jones; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

9.  Synthesis of unsymmetrically substituted biaryls via sequential lithiation of dibromobiaryls using integrated microflow systems.

Authors:  Aiichiro Nagaki; Naofumi Takabayashi; Yutaka Tomida; Jun-ichi Yoshida
Journal:  Beilstein J Org Chem       Date:  2009-04-29       Impact factor: 2.883

10.  The rapid generation of isothiocyanates in flow.

Authors:  Marcus Baumann; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2013-08-08       Impact factor: 2.883

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