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Readily Accessible Bulky Iron Catalysts exhibiting Site Selectivity in the Oxidation of Steroidal Substrates

Bulky iron complexes are described that catalyze the site-selective oxidation of alkyl C-H bonds with hydrogen peroxide under mild conditions. Steric bulk at the iron center is introduced by appending trialkylsilyl groups at the meta-position of the pyridines in tetradentate aminopyridine ligands, and this effect translates into high product yields, an enhanced preferential oxidation of secondary over tertiary C-H bonds, and the ability to perform site-selective oxidation of methylenic sites in terpenoid and steroidal substrates. Unprecedented site selective oxidation at C6 and C12 methylenic sites in steroidal substrates is shown to be governed by the chirality of the catalysts

El mateix article està publicat a l’edició alemanya d’Angewandte Chemie (ISSN 0044-8249 EISSN:1521-3757), 2016, vol.128, núm. 19, p.5870-5873. DOI http://dx.doi.org/10.1002/ange.201600785

Financial support for this work was provided by the European Commission (ERC2009-StG-239910 to M.C.), the Spanish Ministry of Science (CTQ2012-37420-C02-01/BQU to M.C., and Generalitat de Catalunya (SGR862 and ICREA Academia Award to M.C.)

© Angewandte Chemie International Edition, 2016, vol. 55, núm. 19, p. 5776-5779

Wiley

Author: Font Gimbernat, David
Canta i Roldós, Mercè
Milan, Michela
Cussó Forest, Olaf
Ribas Salamaña, Xavi
Klein Gebbink, Robertus J M
Costas Salgueiro, Miquel
Date: 2016
Abstract: Bulky iron complexes are described that catalyze the site-selective oxidation of alkyl C-H bonds with hydrogen peroxide under mild conditions. Steric bulk at the iron center is introduced by appending trialkylsilyl groups at the meta-position of the pyridines in tetradentate aminopyridine ligands, and this effect translates into high product yields, an enhanced preferential oxidation of secondary over tertiary C-H bonds, and the ability to perform site-selective oxidation of methylenic sites in terpenoid and steroidal substrates. Unprecedented site selective oxidation at C6 and C12 methylenic sites in steroidal substrates is shown to be governed by the chirality of the catalysts
El mateix article està publicat a l’edició alemanya d’Angewandte Chemie (ISSN 0044-8249 EISSN:1521-3757), 2016, vol.128, núm. 19, p.5870-5873. DOI http://dx.doi.org/10.1002/ange.201600785
Financial support for this work was provided by the European Commission (ERC2009-StG-239910 to M.C.), the Spanish Ministry of Science (CTQ2012-37420-C02-01/BQU to M.C., and Generalitat de Catalunya (SGR862 and ICREA Academia Award to M.C.)
Format: application/pdf
ISSN: 1433-7851 (versió paper)
1521-3773 (versió electrònica)
Document access: http://hdl.handle.net/10256/12492
Language: eng
Publisher: Wiley
Collection: Reproducció digital del document publicat a: http://dx.doi.org/10.1002/anie.201600785
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/239910
Is part of: © Angewandte Chemie International Edition, 2016, vol. 55, núm. 19, p. 5776-5779
Rights: Tots els drets reservats
Subject: Catàlisi asimètrica
Enantioselective catalysis
Síntesi asimètrica
Asymmetric synthesis
Catalitzadors de ferro
Iron catalysts
Ferro
Iron
Activació (Química)
Activation (Chemistry)
Title: Readily Accessible Bulky Iron Catalysts exhibiting Site Selectivity in the Oxidation of Steroidal Substrates
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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