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Biologically inspired non-heme iron-catalysts for asymmetric epoxidation; Design principles and perspectives

Iron coordination complexes with nitrogen and oxygen donor ligands have long since been known to react with peroxides producing powerful oxidizing species. These compounds can be regarded as simple structural and functional models of the active sites of non-heme iron dependent oxygenases. Research efforts during the last decade have uncovered basic principles and structural coordination chemistry motifs that permit us to control the chemistry that evolves when these iron complexes react with peroxides, in order to provide powerful metal-based, but at the same time selective, oxidising agents. Oxidation methodologies with synthetic value are currently emerging from this approach. The current review focuses on asymmetric epoxidation, a reaction which has large value in synthesis, and where iron/H2O2 based methodologies may represent not only a sustainable choice, but may also expand the scope of state-of-the-art oxidation methods. Basic principles that underlay catalyst design as well as H2O2 activation are discussed, whilst limitations and future perspectives are also reviewed

We acknowledge help from Dr Christopher Whiteoak in proofreading the manuscript and providing valuable suggestions. We acknowledge financial support from the European Research Council (ERC-2009-StG-239910), MINECO of Spain (CTQ2012-37420-C02-01/BQU, CSD2010-00065), and Generalitat de Catalunya (2014 SGR 862). X.R. and M.C. thank ICREA-Academia awards

© Chemical Communications, 2015, vol. 51, núm. 76, p. 14285-14298

Royal Society of Chemistry (RSC)

Author: Cussó Forest, Olaf
Ribas Salamaña, Xavi
Costas Salgueiro, Miquel
Date: 2015
Abstract: Iron coordination complexes with nitrogen and oxygen donor ligands have long since been known to react with peroxides producing powerful oxidizing species. These compounds can be regarded as simple structural and functional models of the active sites of non-heme iron dependent oxygenases. Research efforts during the last decade have uncovered basic principles and structural coordination chemistry motifs that permit us to control the chemistry that evolves when these iron complexes react with peroxides, in order to provide powerful metal-based, but at the same time selective, oxidising agents. Oxidation methodologies with synthetic value are currently emerging from this approach. The current review focuses on asymmetric epoxidation, a reaction which has large value in synthesis, and where iron/H2O2 based methodologies may represent not only a sustainable choice, but may also expand the scope of state-of-the-art oxidation methods. Basic principles that underlay catalyst design as well as H2O2 activation are discussed, whilst limitations and future perspectives are also reviewed
We acknowledge help from Dr Christopher Whiteoak in proofreading the manuscript and providing valuable suggestions. We acknowledge financial support from the European Research Council (ERC-2009-StG-239910), MINECO of Spain (CTQ2012-37420-C02-01/BQU, CSD2010-00065), and Generalitat de Catalunya (2014 SGR 862). X.R. and M.C. thank ICREA-Academia awards
Format: application/pdf
ISSN: 1359-7345 (versió paper)
1364-548X (versió electrònica)
Document access: http://hdl.handle.net/10256/11205
Language: eng
Publisher: Royal Society of Chemistry (RSC)
Collection: MINECO/PN 2013-2015/CTQ2012-37420-C02-01
MICINN/PN 2010-2016/CSD2010-00065
AGAUR/2014-2016/2014 SGR-862
Reproducció digital del document publicat a: http://dx.doi.org/10.1039/c5cc05576h
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/239910
Is part of: © Chemical Communications, 2015, vol. 51, núm. 76, p. 14285-14298
Rights: Tots els drets reservats
Subject: Compostos de coordinació
Coordination compounds
Catalitzadors
Catalysts
Epòxids
Epoxy compounds
Title: Biologically inspired non-heme iron-catalysts for asymmetric epoxidation; Design principles and perspectives
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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