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Haloboration: scope, mechanism and utility

Haloboration, the addition of B–X (X = Cl, Br, I) across an unsaturated moiety e.g., C[double bond, length as m-dash]Y or C[triple bond, length as m-dash]Y (Y = C, N, etc.), is dramatically less utilised than the ubiquitous hydroboration reaction. However, haloboration of alkynes in particular is a...

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Detalles Bibliográficos
Autores principales: Kirschner, Sven, Yuan, Kang, Ingleson, Michael J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8381870/
https://www.ncbi.nlm.nih.gov/pubmed/34483652
http://dx.doi.org/10.1039/d0nj02908d
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author Kirschner, Sven
Yuan, Kang
Ingleson, Michael J.
author_facet Kirschner, Sven
Yuan, Kang
Ingleson, Michael J.
author_sort Kirschner, Sven
collection PubMed
description Haloboration, the addition of B–X (X = Cl, Br, I) across an unsaturated moiety e.g., C[double bond, length as m-dash]Y or C[triple bond, length as m-dash]Y (Y = C, N, etc.), is dramatically less utilised than the ubiquitous hydroboration reaction. However, haloboration of alkynes in particular is a useful tool to access ambiphilic 1,2-disubstituted alkenes. The stereochemical outcome of the reaction is easily controlled and the resulting products have proven to be valuable building blocks in organic synthesis and materials chemistry. This review aims at providing the reader with a brief summary of the historic development and of the current mechanistic understanding of this transformation. Recent developments are discussed and select examples demonstrating the use of haloboration products are given with a focus on the major areas, specifically, natural product synthesis and the development of boron-doped polycyclic aromatic hydrocarbons (B-PAHs).
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spelling pubmed-83818702021-09-01 Haloboration: scope, mechanism and utility Kirschner, Sven Yuan, Kang Ingleson, Michael J. New J Chem Chemistry Haloboration, the addition of B–X (X = Cl, Br, I) across an unsaturated moiety e.g., C[double bond, length as m-dash]Y or C[triple bond, length as m-dash]Y (Y = C, N, etc.), is dramatically less utilised than the ubiquitous hydroboration reaction. However, haloboration of alkynes in particular is a useful tool to access ambiphilic 1,2-disubstituted alkenes. The stereochemical outcome of the reaction is easily controlled and the resulting products have proven to be valuable building blocks in organic synthesis and materials chemistry. This review aims at providing the reader with a brief summary of the historic development and of the current mechanistic understanding of this transformation. Recent developments are discussed and select examples demonstrating the use of haloboration products are given with a focus on the major areas, specifically, natural product synthesis and the development of boron-doped polycyclic aromatic hydrocarbons (B-PAHs). The Royal Society of Chemistry 2020-07-08 /pmc/articles/PMC8381870/ /pubmed/34483652 http://dx.doi.org/10.1039/d0nj02908d Text en This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Kirschner, Sven
Yuan, Kang
Ingleson, Michael J.
Haloboration: scope, mechanism and utility
title Haloboration: scope, mechanism and utility
title_full Haloboration: scope, mechanism and utility
title_fullStr Haloboration: scope, mechanism and utility
title_full_unstemmed Haloboration: scope, mechanism and utility
title_short Haloboration: scope, mechanism and utility
title_sort haloboration: scope, mechanism and utility
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8381870/
https://www.ncbi.nlm.nih.gov/pubmed/34483652
http://dx.doi.org/10.1039/d0nj02908d
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AT yuankang haloborationscopemechanismandutility
AT inglesonmichaelj haloborationscopemechanismandutility