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Angew Chem Int Ed Engl. 2019 Jul 22;58(30):10305-10309. doi: 10.1002/anie.201904263. Epub 2019 Jun 17.

Copper-Catalyzed 1,2-Methoxy Methoxycarbonylation of Alkenes with Methyl Formate.

Angewandte Chemie (International ed. in English)

Balázs Budai, Alexandre Leclair, Qian Wang, Jieping Zhu

Affiliations

  1. Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.

PMID: 31106517 DOI: 10.1002/anie.201904263

Abstract

Reported here is a copper-catalyzed 1,2-methoxy methoxycarbonylation of alkenes by an unprecedented use of methyl formate as a source of both the methoxy and the methoxycarbonyl groups. This reaction transforms styrene and its derivatives into value-added β-methoxy alkanoates and cinnamates, as well as medicinally important five-membered heterocycles, such as functionalized tetrahydrofurans, γ-lactones, and pyrrolidines. A ternary β-diketiminato-Cu

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: alkenes; copper; heterocycles; homogeneous catalysis; radicals

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Grant support