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Pd(II)-Catalyzed Fujiwara-Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins
Verónica Ortiz-de-Elguea1, Asier Carral-Menoyo1, Lorena Simón-Vidal1
1Departamento de Química Orgánica e Inorgánica, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea UPV/EHU, Apdo. 644, Bilbao 48080, Spain.
Abstract:
Highly substituted coumarins, privileged and versatile scaffolds for bioactive natural products and fluorescence imaging, are obtained via a Pd(II)-catalyzed direct C-H alkenylation reaction (Fujiwara-Moritani reaction), which has emerged as a powerful tool for the construction and functionalization of heterocyclic compounds because of its chemical versatility and its environmental advantages. Thus, a selective 6-endo cyclization led to 4-substituted coumarins in moderate yields. Selected examples have been further functionalized in C3 through a second intermolecular C-H alkenylation reaction to give coumarin-acrylate hybrids, whose fluorescence spectra have been measured.
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