Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis

[Image: see text] The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carba...

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Autores principales: Hong, Kai, Liu, Xun, Morken, James P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4353009/
https://www.ncbi.nlm.nih.gov/pubmed/25019925
http://dx.doi.org/10.1021/ja505455z
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author Hong, Kai
Liu, Xun
Morken, James P.
author_facet Hong, Kai
Liu, Xun
Morken, James P.
author_sort Hong, Kai
collection PubMed
description [Image: see text] The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.
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spelling pubmed-43530092015-07-14 Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis Hong, Kai Liu, Xun Morken, James P. J Am Chem Soc [Image: see text] The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion. American Chemical Society 2014-07-14 2014-07-30 /pmc/articles/PMC4353009/ /pubmed/25019925 http://dx.doi.org/10.1021/ja505455z Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Hong, Kai
Liu, Xun
Morken, James P.
Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis
title Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis
title_full Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis
title_fullStr Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis
title_full_unstemmed Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis
title_short Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis
title_sort simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4353009/
https://www.ncbi.nlm.nih.gov/pubmed/25019925
http://dx.doi.org/10.1021/ja505455z
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AT morkenjamesp simpleaccesstoelusiveaborylcarbanionsandtheiralkylationanumpolungconstructionfororganicsynthesis

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