Dearomative Allylation of Naphthyl Cyanohydrins by Palladium Catalysis: Catalyst-Enhanced Site Selectivity.

Author(s) Yanagimoto, A.; Komatsuda, M.; Muto, K.; Yamaguchi, J.
Journal Org Lett
Date Published 2020 Apr 09
Abstract

A dearomative allylation of naphthyl cyanohydrins with allyl borates and allyl stannanes under palladium catalysis was developed. At the initial stage of this study, the dearomative reaction (C4 substitution of the aromatics) was competing with benzyl substitution. To circumvent this issue, the use of palladium and -disubstituted triarylphosphine as the catalyst in a 1:1 ratio was found to enhance the site selectivity, furnishing the desired dearomatized products. Further derivatizations of products were also successful.

DOI 10.1021/acs.orglett.0c00897
ISSN 1523-7052
Citation Org Lett. 2020.