Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes

[Image: see text] A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence...

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Autores principales: Cruz, Daniel A., Sinka, Victoria, de Armas, Pedro, Steingruber, Hugo Sebastian, Fernández, Israel, Martín, Víctor S., Miranda, Pedro O., Padrón, Juan I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8397429/
https://www.ncbi.nlm.nih.gov/pubmed/34318671
http://dx.doi.org/10.1021/acs.orglett.1c02186
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author Cruz, Daniel A.
Sinka, Victoria
de Armas, Pedro
Steingruber, Hugo Sebastian
Fernández, Israel
Martín, Víctor S.
Miranda, Pedro O.
Padrón, Juan I.
author_facet Cruz, Daniel A.
Sinka, Victoria
de Armas, Pedro
Steingruber, Hugo Sebastian
Fernández, Israel
Martín, Víctor S.
Miranda, Pedro O.
Padrón, Juan I.
author_sort Cruz, Daniel A.
collection PubMed
description [Image: see text] A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui’s radical susceptibilities support the obtained results.
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spelling pubmed-83974292021-08-31 Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes Cruz, Daniel A. Sinka, Victoria de Armas, Pedro Steingruber, Hugo Sebastian Fernández, Israel Martín, Víctor S. Miranda, Pedro O. Padrón, Juan I. Org Lett [Image: see text] A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui’s radical susceptibilities support the obtained results. American Chemical Society 2021-07-28 2021-08-06 /pmc/articles/PMC8397429/ /pubmed/34318671 http://dx.doi.org/10.1021/acs.orglett.1c02186 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Cruz, Daniel A.
Sinka, Victoria
de Armas, Pedro
Steingruber, Hugo Sebastian
Fernández, Israel
Martín, Víctor S.
Miranda, Pedro O.
Padrón, Juan I.
Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
title Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
title_full Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
title_fullStr Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
title_full_unstemmed Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
title_short Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
title_sort iron(ii) and copper(i) control the total regioselectivity in the hydrobromination of alkenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8397429/
https://www.ncbi.nlm.nih.gov/pubmed/34318671
http://dx.doi.org/10.1021/acs.orglett.1c02186
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