Literature DB >> 24753266

Multicomponent, flow diazotization/Mizoroki-Heck coupling protocol: dispelling myths about working with diazonium salts.

Kumara S Nalivela1, Michael Tilley, Michael A McGuire, Michael G Organ.   

Abstract

A single pass flow diazotization/Mizoroki-Heck protocol has been developed for the production of cinnimoyl and styryl products. The factors that govern aryl diazonium salt stability have been examined in detail leading to the development of a MeOH/DMF co-solvent system in which the diazonium salts can be generated in the presence of all other reaction components and then coupled selectively to give the desired products. Finally the key role of the reaction quench for flow reactions has been demonstrated.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Heck reaction; cross-coupling; diazonium salts; flow; microreactors

Mesh:

Substances:

Year:  2014        PMID: 24753266     DOI: 10.1002/chem.201402092

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


  3 in total

1.  Practical and economic lithiations of functionalized arenes and heteroarenes using Cy2NLi in the presence of Mg, Zn or La halides in a continuous flow.

Authors:  Matthias R Becker; Maximilian A Ganiek; Paul Knochel
Journal:  Chem Sci       Date:  2015-08-10       Impact factor: 9.825

2.  Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids.

Authors:  Alexander Kremsmair; Andreas Hess; Benjamin Heinz; Paul Knochel
Journal:  Chemistry       Date:  2021-11-29       Impact factor: 5.020

3.  Exploring Flow Procedures for Diazonium Formation.

Authors:  Te Hu; Ian R Baxendale; Marcus Baumann
Journal:  Molecules       Date:  2016-07-14       Impact factor: 4.411

  3 in total

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