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Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis

Yoon Kyung Jang, Tobias Krückel, Magnus Rueping*, Osama El-Sepelgy*

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

Y. K. Jang, T. Krückel, M. Rueping, O. El-Sepelgy, Org. Lett., 2018, 20, 7779-7783.

DOI: 10.1021/acs.orglett.8b03184 (free Supporting Information)



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Abstract

A manganese-catalyzed C-alkylation of carboxylic acid derivatives with alcohols operates via hydrogen autotransfer and ideally produces water as the only side product. Importantly, aliphatic-, benzylic-, and heterocyclic-containing alcohols can be used as alkylating reagents, eliminating the need for mutagenic alkyl halides.

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Key Words

alkylation of amides, benzylation


ID: J54-Y2018