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Cooperative Metal-Ligand Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Allenes Using a Stable Iron Catalyst

Osama El-Sepelgy*, Aleksandra Brzozowska, Jan Sklyaruk, Yoon Kyung Jang, Viktoriia Zubar and Magnus Rueping*

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Email: osama.elsepelgyrwth-aachen.de, magnus.ruepingrwth-aachen.de

O. El-Sepelgy, A. Brzozowska, J. Sklyaruk, Y. K. Jang, V. Zubar, M. Rueping, Org. Lett., 2018, 20, 696-699.

DOI: 10.1021/acs.orglett.7b03828 (free Supporting Information)


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Abstract

A chemoselective intramolecular hydroamination and hydroalkoxylation of readily available α-allenic amines and alcohols provides valuable 2,3-dihydropyrroles and 2,3-dihydrofurans in the presence of low amounts of an air and moisture stable iron catalyst. The mild reaction conditions allow fthe hydrofunctionalization of a wide range of allenes bearing different functional groups in good yields in the absence of base or any sensitive additives.

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proposed mechanism



Key Words

2,3-dihydropyrroles, 2,3-dihydrofurans


ID: J54-Y2018