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

preprint
submitted on 10.03.2020 and posted on 11.03.2020 by Aika Yanagimoto, Masaaki Komatsuda, Kei Muto, Junichiro Yamaguchi
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.

History

Email Address of Submitting Author

junyamaguchi@waseda.jp

Institution

Waseda University

Country

Japan

ORCID For Submitting Author

0000-0002-3896-5882

Declaration of Conflict of Interest

No competing financial interests have been declared.

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