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Org Lett. 2017 Oct 6;19(19):5264-5267. doi: 10.1021/acs.orglett.7b02532. Epub 2017 Sep 12.

Palladium-Catalyzed Aerobic Oxidative Hydroamination of Vinylarenes Using Anilines: A Wacker-Type Amination Pathway.

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1
Center for Metareceptome Research, College of Pharmacy, Chung-Ang University , 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.

Abstract

A palladium-catalyzed intermolecular hydroamination of vinylarene derivatives using anilines has been developed for the first time under aerobic conditions, where the regioselective formation of N-arylketimines is accomplished. The current aerobic oxidative hydroamination pathway of anilines is distinct from that of palladium-catalyzed hydroamination reactions that proceed to give sec-arylethylamine and arylethylamine derivatives, identifying a longstanding missing reaction pathway, Wacker-type amination, to N-arylketimines using anilines. The ready availability of both starting materials, vinylarenes and anilines, offers an attractive and facile synthetic route to N-arylketimines in good to excellent yields.

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