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Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H(2)O(2) Combined with Periodate Oxidation

A one‐pot multi‐step method for the oxidative cleavage of alkenes to aldehydes/ketones under ambient conditions is described as an alternative to ozonolysis. The first step is a highly efficient manganese catalyzed epoxidation/cis‐dihydroxylation of alkenes. This step is followed by an Fe(III) assis...

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Autores principales: Mecozzi, Francesco, Dong, Jia Jia, Angelone, Davide, Browne, Wesley R., Eisink, Niek N. H. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6899713/
https://www.ncbi.nlm.nih.gov/pubmed/31866758
http://dx.doi.org/10.1002/ejoc.201901380
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author Mecozzi, Francesco
Dong, Jia Jia
Angelone, Davide
Browne, Wesley R.
Eisink, Niek N. H. M.
author_facet Mecozzi, Francesco
Dong, Jia Jia
Angelone, Davide
Browne, Wesley R.
Eisink, Niek N. H. M.
author_sort Mecozzi, Francesco
collection PubMed
description A one‐pot multi‐step method for the oxidative cleavage of alkenes to aldehydes/ketones under ambient conditions is described as an alternative to ozonolysis. The first step is a highly efficient manganese catalyzed epoxidation/cis‐dihydroxylation of alkenes. This step is followed by an Fe(III) assisted ring opening of the epoxide (where necessary) to a 1,2‐diol. Carbon–carbon bond cleavage is achieved by treatment of the diol with sodium periodate. The conditions used in each step are not only compatible with the subsequent step(s), but also provide for increased conversion compared to the equivalent reactions carried out on the isolated intermediate compounds. The described procedure allows for carbon–carbon bond cleavage in the presence of other alkenes, oxidation sensitive moieties and other functional groups; the mild conditions (r.t.) used in all three steps make this a viable general alternative to ozonolysis and especially for use under flow or continuous batch conditions.
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spelling pubmed-68997132019-12-19 Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H(2)O(2) Combined with Periodate Oxidation Mecozzi, Francesco Dong, Jia Jia Angelone, Davide Browne, Wesley R. Eisink, Niek N. H. M. European J Org Chem Full Papers A one‐pot multi‐step method for the oxidative cleavage of alkenes to aldehydes/ketones under ambient conditions is described as an alternative to ozonolysis. The first step is a highly efficient manganese catalyzed epoxidation/cis‐dihydroxylation of alkenes. This step is followed by an Fe(III) assisted ring opening of the epoxide (where necessary) to a 1,2‐diol. Carbon–carbon bond cleavage is achieved by treatment of the diol with sodium periodate. The conditions used in each step are not only compatible with the subsequent step(s), but also provide for increased conversion compared to the equivalent reactions carried out on the isolated intermediate compounds. The described procedure allows for carbon–carbon bond cleavage in the presence of other alkenes, oxidation sensitive moieties and other functional groups; the mild conditions (r.t.) used in all three steps make this a viable general alternative to ozonolysis and especially for use under flow or continuous batch conditions. John Wiley and Sons Inc. 2019-10-31 2019-11-14 /pmc/articles/PMC6899713/ /pubmed/31866758 http://dx.doi.org/10.1002/ejoc.201901380 Text en © 2019 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Full Papers
Mecozzi, Francesco
Dong, Jia Jia
Angelone, Davide
Browne, Wesley R.
Eisink, Niek N. H. M.
Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H(2)O(2) Combined with Periodate Oxidation
title Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H(2)O(2) Combined with Periodate Oxidation
title_full Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H(2)O(2) Combined with Periodate Oxidation
title_fullStr Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H(2)O(2) Combined with Periodate Oxidation
title_full_unstemmed Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H(2)O(2) Combined with Periodate Oxidation
title_short Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H(2)O(2) Combined with Periodate Oxidation
title_sort oxidative cleavage of alkene c=c bonds using a manganese catalyzed oxidation with h(2)o(2) combined with periodate oxidation
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6899713/
https://www.ncbi.nlm.nih.gov/pubmed/31866758
http://dx.doi.org/10.1002/ejoc.201901380
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