Synthesis 2016; 48(03): 340-350
DOI: 10.1055/s-0035-1560909
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© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed C-Allylating Partial Dearomatization of Naphthols

Berenice Heid, Bernd Plietker*
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Publication History

Received: 18 September 2015

Accepted after revision: 16 October 2015

Publication Date:
25 November 2015 (eFirst)

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.

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