The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols

We describe herein the design of a novel molecular scaffold that can induce facile oxidative olefinations when attached to alcohols. Benzylic, homo-, and bishomobenzylic alcohols are utilized. The scaffold can act as a protecting group for the alcohol in other transformations, and it is recoverable...

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Detalles Bibliográficos
Autores principales: Knight, Brian J., Rothbaum, Jacob O., Ferreira, Eric M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5966905/
https://www.ncbi.nlm.nih.gov/pubmed/29899921
http://dx.doi.org/10.1039/c5sc03948g
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author Knight, Brian J.
Rothbaum, Jacob O.
Ferreira, Eric M.
author_facet Knight, Brian J.
Rothbaum, Jacob O.
Ferreira, Eric M.
author_sort Knight, Brian J.
collection PubMed
description We describe herein the design of a novel molecular scaffold that can induce facile oxidative olefinations when attached to alcohols. Benzylic, homo-, and bishomobenzylic alcohols are utilized. The scaffold can act as a protecting group for the alcohol in other transformations, and it is recoverable in excellent yield. The overall sequence can also be telescoped without purifications of intermediates, representing a net alcohol-based directed ortho-alkenylation.
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spelling pubmed-59669052018-06-13 The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols Knight, Brian J. Rothbaum, Jacob O. Ferreira, Eric M. Chem Sci Chemistry We describe herein the design of a novel molecular scaffold that can induce facile oxidative olefinations when attached to alcohols. Benzylic, homo-, and bishomobenzylic alcohols are utilized. The scaffold can act as a protecting group for the alcohol in other transformations, and it is recoverable in excellent yield. The overall sequence can also be telescoped without purifications of intermediates, representing a net alcohol-based directed ortho-alkenylation. Royal Society of Chemistry 2016-03-01 2015-12-14 /pmc/articles/PMC5966905/ /pubmed/29899921 http://dx.doi.org/10.1039/c5sc03948g Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Knight, Brian J.
Rothbaum, Jacob O.
Ferreira, Eric M.
The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols
title The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols
title_full The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols
title_fullStr The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols
title_full_unstemmed The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols
title_short The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols
title_sort design of a readily attachable and cleavable molecular scaffold for ortho-selective c–h alkenylation of arene alcohols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5966905/
https://www.ncbi.nlm.nih.gov/pubmed/29899921
http://dx.doi.org/10.1039/c5sc03948g
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