Copper-Mediated N-Arylations of Hydantoins

MINAKEM RECHERCHE has collaborated with the research group of Prof. Gwilherm Evano, from the ULB to develop a flexible approach towards N-arylated hydantoins. We are very pleased to announce that the publication has been approved in the Journal of Organic Chemistry.

Abstract

A set of two efficient and broadly applicable procedures for the N-arylation of hydantoins at the two nitrogen atoms is reported. The first one relies on the use of stoichiometric amounts of copper(I) oxide under ligandless and base-free conditions and enables a clean and regioselective arylation at the N3 nitrogen atom while the second one is based on the use of catalytic amounts of copper(I) iodide and trans-N, N′-dimethylcyclohexane -1,2-diamine and promotes arylation at the N1 nitrogen atom. Importantly, the combination of these two procedures affords a straightforward and general entry to diarylated hydantoins.

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AuthorsPierre ThilmanyPhidéline GérardAgathe VanoostChristopher DeldaeleLaurent Petit, and Gwilherm Evano

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Source:  J. Org. Chem., Just Accepted Manuscript
DOI10.1021/acs.joc.8b02284
Publication Date (Web): November 9, 2018
Copyright © 2018 American Chemical Society

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