Campus Units

Chemistry, NSF Engineering Research Center for Biorenewable Chemicals

Document Type

Article

Publication Version

Accepted Manuscript

Publication Date

9-15-2014

Journal or Book Title

RSC Advances

Volume

4

Issue

86

First Page

45657

Last Page

45664

DOI

10.1039/C4RA07105K

Abstract

The conversion of naturally-occurring malic acid to the 2-pyrone methyl coumalate was optimized using a variety of acid catalysts. Coupling methyl coumalate with electron-rich dienophiles in an inverse electron-demand Diels–Alder (IEDDA)/decarboxylation/elimination domino sequence resulted in an investigation of the scope and limitations of the methodology. The thermal, metal-free, and one-pot procedure allows regioselective access to diverse aromatic compounds including tricyclic, biphenyl, and pyridinyl systems for elaboration. A comparison with analogous pyrones demonstrates the striking efficacy of methyl coumalate as a versatile platform for the generation of biorenewable functionalized benzoates.

Comments

This is a manuscript of an article published as Lee, Jennifer J., Gerald R. Pollock III, Donald Mitchell, Lindsay Kasuga, and George A. Kraus. "Upgrading malic acid to bio-based benzoates via a Diels–Alder-initiated sequence with the methyl coumalate platform." RSC Advances 4, no. 86 (2014): 45657-45664. DOI: 10.1039/C4RA07105K. Posted with permission.

Copyright Owner

The Royal Society of Chemistry

Language

en

File Format

application/pdf

Published Version

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