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

11 March 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A dearomative allylation of aromatic 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 meta-disubstituted triarylphosphine as the catalyst in a 1:1 ratio was found to enhance the site-selectivity, furnishing the desired dearomatized products. As the products possess an unsaturated nitrile moiety, further derivatizations of products such as conjugate additions and reductions were achieved.

Keywords

Palladium Catalysis
Dearomatization Reactions
cyanohydrins

Supplementary materials

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Title
Yanagimoto SI 20200310
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