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Ligand and pH Influence on Manganese-Mediated Peracetic Acid Epoxidation of Terminal Olefins
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Abstract
Nineteen MnII complexes were screened for the catalytic epoxidation of terminal olefins using peracetic acid. Few of these complexes are efficient catalysts at pH < 2, but many are effective at 1 mol % catalyst loading at pH 4. With 0.1 mol % loading, four complexes epoxidize 1-octene in 
80% yield in 5 min. The relative reactivity of the catalysts toward different olefins was probed using a multicomponent intermolecular competition reaction.
Citing Articles
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This article has been cited by 12 ACS Journal articles (5 most recent appear below).
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 ...
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 ...
Efficient and Selective Peracetic Acid Epoxidation Catalyzed by a Robust Manganese Catalyst
Isaac Garcia-Bosch, Anna Company, Xavier Fontrodona, Xavi Ribas and Miquel CostasOrganic Letters2008 10 (11), 2095-2098Efficient and Selective Peracetic Acid Epoxidation Catalyzed by a Robust Manganese Catalyst
Isaac Garcia-Bosch, Anna Company, Xavier Fontrodona, Xavi Ribas and Miquel CostasOrganic Letters2008 10 (11), 2095-2098A manganese catalyst containing a tetradentate ligand derived from triazacyclononane exhibits high catalytic activity in epoxidation reactions using peracetic acid as oxidant. The system exhibits broad substrate scope and requires small (0.1−0.15 mol %) ...
Utilization of a Michael Addition: Dipolar Cycloaddition Cascade for the Synthesis of (±)-Cylindricine C
Andrew C. Flick, Maria José Arevalo Caballero and Albert PadwaOrganic Letters2008 10 (9), 1871-1874Utilization of a Michael Addition: Dipolar Cycloaddition Cascade for the Synthesis of (±)-Cylindricine C
Andrew C. Flick, Maria José Arevalo Caballero and Albert PadwaOrganic Letters2008 10 (9), 1871-1874A new approach to the marine alkaloid (±)-cylindricine C has been devised. The key element of the synthesis consists of a Michael addition/dipolar cycloaddition cascade between 2,3-bis(phenylsulfonyl)-1,3-butadiene and 9-triisopropylsilanyloxy-non-1-en-...
Covalent Heterogenization of a Discrete Mn(II) Bis-Phen Complex by a Metal-Template/Metal-Exchange Method: An Epoxidation Catalyst with Enhanced Reactivity
Tracy J. Terry and T. Daniel P. StackJournal of the American Chemical Society2008 130 (14), 4945-4953Covalent Heterogenization of a Discrete Mn(II) Bis-Phen Complex by a Metal-Template/Metal-Exchange Method: An Epoxidation Catalyst with Enhanced Reactivity
Tracy J. Terry and T. Daniel P. StackJournal of the American Chemical Society2008 130 (14), 4945-4953Considerable attention has been devoted to the immobilization of discrete epoxidation catalysts onto solid supports due to the possible benefits of site isolation such as increased catalyst stability, catalyst recycling, and product separation. A ...
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History
- Published In Issue September 02, 2004
- Received June 17, 2004
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