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Renewable solvents for palladium-catalyzed carbonylation reactions

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DOI

  • Aya Ismael, UiT The Arctic University of Norway
  • ,
  • Ashot Gevorgyan, UiT The Arctic University of Norway
  • ,
  • Troels Skrydstrup
  • Annette Bayer, UiT The Arctic University of Norway

Solvents constitute the largest component for many chemical processes and substitution of nonrenewable solvents is a longstanding goal for green chemistry. Here, we show that Pd-catalyzed carbonylative couplings, such as carbonylative crosscouplings, aminocarbonylations, and alkoxycarbonylations, can be successfully realized using renewable solvents. The present research covers not only well-established renewable solvents, such as 2-methyltetrahydrofuran (2MeTHF), limonene, and dimethyl carbonate, but also recently introduced biomass-derived 1,1-diethoxyethane, isosorbide dimethyl ether, eucalyptol, rose oxide, γ-terpinene, and α-pinene. The carbonylative coupling of boronic acids and aryl bromides works well in limonene. Aminocarbonylation gave excellent results in dimethyl carbonate, α-pinene, and limonene, while alkoxycarbonylation was successful in 2MeTHF, α-pinene, γ-terpinene, and dimethyl carbonate. The developed methods based on renewable solvents can be used for the synthesis of commercial drug Trimetozine and an analogue of Itopride.

Original languageEnglish
JournalOrganic Process Research and Development
Volume24
Issue11
Pages (from-to)2665-2675
Number of pages11
ISSN1083-6160
DOIs
Publication statusPublished - 20 Nov 2020

Bibliographical note

Publisher Copyright:
© 2020 American Chemical Society.

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

    Research areas

  • Alkoxycarbonylation, Aminocarbonylation, Carbon monoxide, Carbonylative C-C coupling, Palladium catalysis, Renewable solvents

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