Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants

Dirhodium(II) complexes and iodine(III) oxidants have found useful applications in synthetic nitrene chemistry. In this study, the combination of the dirhodium(II) complex Rh2(tpa)4 (tpa = triphenylacetate) with the iodine(III) oxidant PhI(OPiv)2 is shown to promote the epoxidation of alkenes in the...

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Autores principales: Nasrallah, A., Grelier, G., Lapuh, M.I., Duran, F.J., Darses, B., Dauban, P.
Formato: JOUR
Materias:
Alkenes
Epoxidation
Hypervalent Iodine
Lewis acids
Rhodium
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_1434193X_v2018_n42_p5836_Nasrallah
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_1434193X_v2018_n42_p5836_Nasrallah
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spelling todo:paper_1434193X_v2018_n42_p5836_Nasrallah2023-10-03T16:14:14Z Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants Nasrallah, A. Grelier, G. Lapuh, M.I. Duran, F.J. Darses, B. Dauban, P. Alkenes Epoxidation Hypervalent Iodine Lewis acids Rhodium Dirhodium(II) complexes and iodine(III) oxidants have found useful applications in synthetic nitrene chemistry. In this study, the combination of the dirhodium(II) complex Rh2(tpa)4 (tpa = triphenylacetate) with the iodine(III) oxidant PhI(OPiv)2 is shown to promote the epoxidation of alkenes in the presence of 2 equivalents of water. The reaction can be applied to diversely substituted alkenes and the corresponding epoxides are isolated with yields of up to 90 %. A possible mechanism involves the dirhodium(II) complex as a Lewis acid species that would tune the oxidizing character of the iodine(III) reagent. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_1434193X_v2018_n42_p5836_Nasrallah
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Alkenes
Epoxidation
Hypervalent Iodine
Lewis acids
Rhodium
spellingShingle Alkenes
Epoxidation
Hypervalent Iodine
Lewis acids
Rhodium
Nasrallah, A.
Grelier, G.
Lapuh, M.I.
Duran, F.J.
Darses, B.
Dauban, P.
Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants
topic_facet Alkenes
Epoxidation
Hypervalent Iodine
Lewis acids
Rhodium
description Dirhodium(II) complexes and iodine(III) oxidants have found useful applications in synthetic nitrene chemistry. In this study, the combination of the dirhodium(II) complex Rh2(tpa)4 (tpa = triphenylacetate) with the iodine(III) oxidant PhI(OPiv)2 is shown to promote the epoxidation of alkenes in the presence of 2 equivalents of water. The reaction can be applied to diversely substituted alkenes and the corresponding epoxides are isolated with yields of up to 90 %. A possible mechanism involves the dirhodium(II) complex as a Lewis acid species that would tune the oxidizing character of the iodine(III) reagent. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
format JOUR
author Nasrallah, A.
Grelier, G.
Lapuh, M.I.
Duran, F.J.
Darses, B.
Dauban, P.
author_facet Nasrallah, A.
Grelier, G.
Lapuh, M.I.
Duran, F.J.
Darses, B.
Dauban, P.
author_sort Nasrallah, A.
title Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants
title_short Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants
title_full Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants
title_fullStr Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants
title_full_unstemmed Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants
title_sort dirhodium(ii)-mediated alkene epoxidation with iodine(iii) oxidants
url http://hdl.handle.net/20.500.12110/paper_1434193X_v2018_n42_p5836_Nasrallah
work_keys_str_mv AT nasrallaha dirhodiumiimediatedalkeneepoxidationwithiodineiiioxidants
AT grelierg dirhodiumiimediatedalkeneepoxidationwithiodineiiioxidants
AT lapuhmi dirhodiumiimediatedalkeneepoxidationwithiodineiiioxidants
AT duranfj dirhodiumiimediatedalkeneepoxidationwithiodineiiioxidants
AT darsesb dirhodiumiimediatedalkeneepoxidationwithiodineiiioxidants
AT daubanp dirhodiumiimediatedalkeneepoxidationwithiodineiiioxidants
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