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Green Processing and Synthesis

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Microwave heating and conventionally-heated continuous-flow processing as tools for performing cleaner palladium-catalyzed decarboxylative couplings using oxygen as the oxidant – a proof of principle study

DiAndra M. Rudzinski
  • Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, USA
/ Nicholas E. Leadbeater
  • Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, USA
  • :
Published Online: 2013-07-27 | DOI: https://doi.org/10.1515/gps-2013-0043

Abstract

A microwave unit interfaced with a gas-loading accessory is used as a tool for facilitating the palladium-catalyzed decarboxylative Heck reaction of 2,6-dimethoxybenzoic acid and methyl acrylate, using molecular oxygen as the oxidant. The reaction is complete in less time and at a lower catalyst loading than when using conventional approaches. The reaction is scaled up using continuous-flow processing, employing a reactor in which both gas input and heating can be performed simultaneously. An 86% isolated product yield is obtained. This proof-of-principle study paves the way for the technology to be used in other cases of these increasingly popular decarboxylative coupling reactions.

Keywords: decarboxylative coupling; flow chemistry; microwave heating

DiAndra M. Rudzinski

DiAndra M. Rudzinski earned a BS in Chemistry in 2010 at Niagara University in New York State, where she contributed to three peer-reviewed articles. In 2013, under the advisement of Dr. Nicholas E. Leadbeater, she received a Research Master’s Degree in synthetic organic chemistry, from the University of Connecticut. Her research was focused on new organofluorine chemistry, including the formation of trifluoromethyl ketones from Weinreb amide precursors. She also explored the use of microwave and continuous-flow technologies as tools for cleaner and greener metal catalyzed-cyanation and decarboxylative Heck reactions. After an internship at Boehringer-Ingelheim (Ridgefield, CT), she accepted a position at CheminPharma (Farmington, CT) where she is currently employed as a medicinal chemist.

Nicholas E. Leadbeater

Dr. Nicholas E. Leadbeater is currently an Associate Professor at the University of Connecticut in the USA. The overarching theme of his research group is the development of new methods for synthetic chemistry and the use of new technology in both research chemistry and in the undergraduate teaching laboratory. The group’s current hot topics are clean, green oxidation methods, the selective incorporation of fluorine into organic molecules, and the application of flow processing in synthetic chemistry.

Corresponding author: Nicholas E. Leadbeater, Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, USA


Received: 2013-05-30

Accepted: 2013-06-28

Published Online: 2013-07-27

Published in Print: 2013-03-01


Citation Information: Green Processing and Synthesis. Volume 2, Issue 4, Pages 323–328, ISSN (Online) 2191-9550, ISSN (Print) 2191-9542, DOI: https://doi.org/10.1515/gps-2013-0043, July 2013

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