Substituted aromatic compounds are pervasive across a wide spectrum of applications from materials science to the pharmaceutical industry. A newly developed methodology employs a thermal inverse electron-demand Diels-Alder reaction between the renewable diene methyl coumalate and electron-rich dienophiles. The reaction offers practical advantages as it utilizes readily accessible and stable vinyl ether, ketal, or orthoester dienophiles and methyl coumalate. Furthermore, the matched substrates allow a regioselective high-yielding, single-pot transformation in which a Diels-Alder reaction, decarboxylation, and aromatization through elimination result in functionalized aromatic systems. The versatile route provides an alternative, metal-free approach to access a vast array of valuable biologically active materials and specialty chemicals.

Inverse electron-demand Diels-Alder reaction between methyl coumalate and electron-rich dienophiles toward functionalized aromatics

246th National Meeting (2013)

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