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Efficient Epoxidation of Electron-Deficient Olefins with a Cationic Manganese Complex
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Abstract
The complex [MnII(R,R-mcp)(CF3SO3)2] is an efficient and practical catalyst for the epoxidation of electron-deficient olefins. This catalyst is capable of epoxidizing olefins with as little as 0.1 mol % catalyst in under 5 min using 1.2 equiv of peracetic acid as the terminal oxidant. A wide scope of substrates are epoxidized including terminal, tertiary, cis and trans internal, enones, and methacrylates with >85% isolated yields.
Citing Articles
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This article has been cited by 24 ACS Journal articles (5 most recent appear below).
A Highly Reactive Mononuclear Non-Heme Manganese(IV)–Oxo Complex That Can Activate the Strong C–H Bonds of Alkanes
Xiujuan Wu, Mi Sook Seo, Katherine M. Davis, Yong-Min Lee, Junying Chen, Kyung-Bin Cho, Yulia N. Pushkar, and Wonwoo NamJournal of the American Chemical Society2011 133 (50), 20088-20091A Highly Reactive Mononuclear Non-Heme Manganese(IV)–Oxo Complex That Can Activate the Strong C–H Bonds of Alkanes
Xiujuan Wu, Mi Sook Seo, Katherine M. Davis, Yong-Min Lee, Junying Chen, Kyung-Bin Cho, Yulia N. Pushkar, and Wonwoo NamJournal of the American Chemical Society2011 133 (50), 20088-20091A mononuclear non-heme manganese(IV)–oxo complex has been synthesized and characterized using various spectroscopic methods. The Mn(IV)–oxo complex shows high reactivity in oxidation reactions, such as C–H bond activation, oxidations of olefins, alcohols, ...
Steric Modifications Tune the Regioselectivity of the Alkane Oxidation Catalyzed by Non-Heme Iron Complexes
Yu He, John D. Gorden, and Christian R. GoldsmithInorganic Chemistry2011 50 (24), 12651-12660Steric Modifications Tune the Regioselectivity of the Alkane Oxidation Catalyzed by Non-Heme Iron Complexes
Yu He, John D. Gorden, and Christian R. GoldsmithInorganic Chemistry2011 50 (24), 12651-12660Iron complexes with the tetradentate N-donor ligand N,N′-di(phenylmethyl)-N,N′-bis(2-pyridinylmethyl)-1,2-cyclohexanediamine (bbpc) are reported. Despite the benzyl groups present on the amines, the iron compounds catalyze the oxygenation of cyclohexane ...
Nonheme Manganese-Catalyzed Asymmetric Oxidation. A Lewis Acid Activation versus Oxygen Rebound Mechanism: Evidence for the “Third Oxidant”
Roman V. Ottenbacher, Konstantin P. Bryliakov, and Evgenii P. TalsiInorganic Chemistry2010 49 (18), 8620-8628Nonheme Manganese-Catalyzed Asymmetric Oxidation. A Lewis Acid Activation versus Oxygen Rebound Mechanism: Evidence for the “Third Oxidant”
Roman V. Ottenbacher, Konstantin P. Bryliakov, and Evgenii P. TalsiInorganic Chemistry2010 49 (18), 8620-8628The catalytic properties of a series of chiral nonheme aminopyridinylmanganese(II) complexes [LMnII(OTf)2] were investigated. The above complexes were found to efficiently catalyze enantioselective olefin oxidation to the corresponding epoxides with ...
A Series of Peroxomanganese(III) Complexes Supported by Tetradentate Aminopyridyl Ligands: Detailed Spectroscopic and Computational Studies
Robert A. Geiger, Swarup Chattopadhyay, Victor W. Day and Timothy A. JacksonJournal of the American Chemical Society2010 132 (8), 2821-2831A Series of Peroxomanganese(III) Complexes Supported by Tetradentate Aminopyridyl Ligands: Detailed Spectroscopic and Computational Studies
Robert A. Geiger, Swarup Chattopadhyay, Victor W. Day and Timothy A. JacksonJournal of the American Chemical Society2010 132 (8), 2821-2831A set of four [MnII(L7py2R)]2+ complexes, supported by the tetradentate 1,4-bis(2-pyridylmethyl)-1,4-diazepane ligand and derivatives with pyridine substituents in the 5 (R = Br) and 6 positions (R = Me and MeO), are reported. X-ray crystal structures of ...
Asymmetric Epoxidation of Olefins with Chiral Bioinspired Manganese Complexes
Mei Wu, Bin Wang, Shoufeng Wang, Chungu Xia and Wei SunOrganic Letters2009 11 (16), 3622-3625Asymmetric Epoxidation of Olefins with Chiral Bioinspired Manganese Complexes
Mei Wu, Bin Wang, Shoufeng Wang, Chungu Xia and Wei SunOrganic Letters2009 11 (16), 3622-3625A novel series of chiral tetradentate N4 ligands together with their manganese complexes have been designed and synthesized. With 1 mol % manganese catalyst loading, the enantioselective epoxidation of olefins proceeds with nearly full conversion and ...
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History
- Published In Issue May 07, 2003
- Received December 30, 2002
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