Palladium-catalyzed dearomative syn-1,4-oxyamination and carboamination protocol using readily available arenes has been developed. This one-pot procedure utilizes arene-arenophile para-cycloadducts, formed via visible-light-mediated [4+2]-photocycloaddition, which are treated with oxygen or carbon nucleophile via formal allylic substitution to provide direct access to syn-1,4-oxyamination and carboamination products. The reaction conditions permit a wide range of arenes, including both naphthalene derivatives and benzene, as well as nucleophiles (oximes, benzyl alcohols, Grignard reagents). Moreover, this process can be used for asymmetric dearomatization, delivering products with high enantioselectivity. The products are able to go through further derivatization reactions to give new functionalities, even natural products and drugs. Overall, both novel dearomative functionalizations offer straightforward access to complex structures from simple arenes, enabling the rapid formation of highly functionalized building blocks that are otherwise difficult to prepare.

Palladium-catalyzed dearomative syn-1,4-oxyamination and carboamination

2019 Spring National Meeting

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