Iron-Catalyzed C-Allylating Partial Dearomatization of Naphthols
Received: 18 September 2015
Accepted after revision: 16 October 2015
25 November 2015 (eFirst)
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.