Iron-Catalyzed C-Allylating Partial Dearomatization of Naphthols

Abstract

The iron complex Bu₄N[Fe(CO)₃(NO)] (TBA[Fe]) catalyzes the intermolecular allylation of naphthol derivatives to give the corresponding partially dearomatized allylated chromenones in good to excellent yields. The scope and limitations are reported. An efficient decarboxylative intramolecular C-allylation, starting from allyl naphthyl carbonates, was developed. From a mechanistic point of view, the overall process is the result of a fast O-allylation followed by a sigmatropic rearrangement to the desired product.

Key words

iron catalysis - allylation - decarboxylation - dearomatization - substitution - rearrangement

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