Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation

[Image: see text] A magnesium-catalyzed regiodivergent C–O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Expe...

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Autores principales: Magre, Marc, Paffenholz, Eva, Maity, Bholanath, Cavallo, Luigi, Rueping, Magnus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7458426/
https://www.ncbi.nlm.nih.gov/pubmed/32658463
http://dx.doi.org/10.1021/jacs.0c05917
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author Magre, Marc
Paffenholz, Eva
Maity, Bholanath
Cavallo, Luigi
Rueping, Magnus
author_facet Magre, Marc
Paffenholz, Eva
Maity, Bholanath
Cavallo, Luigi
Rueping, Magnus
author_sort Magre, Marc
collection PubMed
description [Image: see text] A magnesium-catalyzed regiodivergent C–O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C–O bond activation and product formation.
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spelling pubmed-74584262020-09-01 Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation Magre, Marc Paffenholz, Eva Maity, Bholanath Cavallo, Luigi Rueping, Magnus J Am Chem Soc [Image: see text] A magnesium-catalyzed regiodivergent C–O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C–O bond activation and product formation. American Chemical Society 2020-07-13 2020-08-19 /pmc/articles/PMC7458426/ /pubmed/32658463 http://dx.doi.org/10.1021/jacs.0c05917 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Magre, Marc
Paffenholz, Eva
Maity, Bholanath
Cavallo, Luigi
Rueping, Magnus
Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation
title Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation
title_full Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation
title_fullStr Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation
title_full_unstemmed Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation
title_short Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation
title_sort regiodivergent hydroborative ring opening of epoxides via selective c–o bond activation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7458426/
https://www.ncbi.nlm.nih.gov/pubmed/32658463
http://dx.doi.org/10.1021/jacs.0c05917
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AT cavalloluigi regiodivergenthydroborativeringopeningofepoxidesviaselectivecobondactivation
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