Synthesis of 1,3‐Bis‐(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2‐Migration

A general and efficient approach for the preparation of 1,3‐bis‐(boryl)alkanes is introduced. It is shown that readily generated vinylboron ate complexes react with commercially available ICH(2)Bpin to valuable 1,3‐bis‐(boryl)alkanes. The introduced transformation, which is experimentally easy to co...

Descripción completa

Detalles Bibliográficos
Autores principales: You, Cai, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7540398/
https://www.ncbi.nlm.nih.gov/pubmed/32579295
http://dx.doi.org/10.1002/anie.202007541
_version_ 1783591199030902784
author You, Cai
Studer, Armido
author_facet You, Cai
Studer, Armido
author_sort You, Cai
collection PubMed
description A general and efficient approach for the preparation of 1,3‐bis‐(boryl)alkanes is introduced. It is shown that readily generated vinylboron ate complexes react with commercially available ICH(2)Bpin to valuable 1,3‐bis‐(boryl)alkanes. The introduced transformation, which is experimentally easy to conduct, shows broad substrate scope and high functional‐group tolerance. Mechanistic studies reveal that the reaction does not proceed via radical intermediates. Instead, an unprecedented boronic ester induced sequential bis‐1,2‐migration cascade is suggested.
format Online
Article
Text
id pubmed-7540398
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-75403982020-10-09 Synthesis of 1,3‐Bis‐(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2‐Migration You, Cai Studer, Armido Angew Chem Int Ed Engl Communications A general and efficient approach for the preparation of 1,3‐bis‐(boryl)alkanes is introduced. It is shown that readily generated vinylboron ate complexes react with commercially available ICH(2)Bpin to valuable 1,3‐bis‐(boryl)alkanes. The introduced transformation, which is experimentally easy to conduct, shows broad substrate scope and high functional‐group tolerance. Mechanistic studies reveal that the reaction does not proceed via radical intermediates. Instead, an unprecedented boronic ester induced sequential bis‐1,2‐migration cascade is suggested. John Wiley and Sons Inc. 2020-08-07 2020-09-21 /pmc/articles/PMC7540398/ /pubmed/32579295 http://dx.doi.org/10.1002/anie.202007541 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
You, Cai
Studer, Armido
Synthesis of 1,3‐Bis‐(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2‐Migration
title Synthesis of 1,3‐Bis‐(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2‐Migration
title_full Synthesis of 1,3‐Bis‐(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2‐Migration
title_fullStr Synthesis of 1,3‐Bis‐(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2‐Migration
title_full_unstemmed Synthesis of 1,3‐Bis‐(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2‐Migration
title_short Synthesis of 1,3‐Bis‐(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2‐Migration
title_sort synthesis of 1,3‐bis‐(boryl)alkanes through boronic ester induced consecutive double 1,2‐migration
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7540398/
https://www.ncbi.nlm.nih.gov/pubmed/32579295
http://dx.doi.org/10.1002/anie.202007541
work_keys_str_mv AT youcai synthesisof13bisborylalkanesthroughboronicesterinducedconsecutivedouble12migration
AT studerarmido synthesisof13bisborylalkanesthroughboronicesterinducedconsecutivedouble12migration

Ejemplares similares