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Palladium-Catalyzed ortho-C-H Alkoxycarbonylation of Aromatic Aldehydes via a Transient Directing Group Strategy
Shanshan Liu1, Sébastien Prévost1
1Laboratoire de Synthèse Organique (LSO - UMR 7652), CNRS, Ecole Polytechnique, ENSTA Paris, Institut Polytechnique de Paris, 828 boulevard des Maréchaux, 91120 Palaiseau, France.
Abstract:
Transient directing groups (TDGs) can be a powerful strategy for directly functionalizing C-H bonds of aldehydes. We report a palladium-catalyzed o-C-H alkoxycarbonylation of benzaldehydes using a catalytic amount of aromatic amine to form a transient imine that plays the role of a monodentate TDG. The reaction conditions were applied to a broad range of aldehydes, and the corresponding 2-formyl benzoates were used as direct precursors for the synthesis of phthalides and 1-isoindolinones.
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