1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans

[Image: see text] A regioselective transition metal-catalyzed cycloisomerization reaction of boron-containing alkynyl epoxides toward C2- and C3-borylated furans has been developed. It was found that the copper catalyst as well as the gold catalyst with more basic triflate counterion favor boryl mig...

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Autores principales: Shiroodi, Roohollah Kazem, Koleda, Olesja, Gevorgyan, Vladimir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183646/
https://www.ncbi.nlm.nih.gov/pubmed/25198147
http://dx.doi.org/10.1021/ja507054j
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author Shiroodi, Roohollah Kazem
Koleda, Olesja
Gevorgyan, Vladimir
author_facet Shiroodi, Roohollah Kazem
Koleda, Olesja
Gevorgyan, Vladimir
author_sort Shiroodi, Roohollah Kazem
collection PubMed
description [Image: see text] A regioselective transition metal-catalyzed cycloisomerization reaction of boron-containing alkynyl epoxides toward C2- and C3-borylated furans has been developed. It was found that the copper catalyst as well as the gold catalyst with more basic triflate counterion favor boryl migration toward C3-borylated furans, whereas employment of the cationic gold hexafluoroantimonate affords C2-borylated furan via a formal 1,2-hydrogen shift.
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spelling pubmed-41836462015-09-08 1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans Shiroodi, Roohollah Kazem Koleda, Olesja Gevorgyan, Vladimir J Am Chem Soc [Image: see text] A regioselective transition metal-catalyzed cycloisomerization reaction of boron-containing alkynyl epoxides toward C2- and C3-borylated furans has been developed. It was found that the copper catalyst as well as the gold catalyst with more basic triflate counterion favor boryl migration toward C3-borylated furans, whereas employment of the cationic gold hexafluoroantimonate affords C2-borylated furan via a formal 1,2-hydrogen shift. American Chemical Society 2014-09-08 2014-09-24 /pmc/articles/PMC4183646/ /pubmed/25198147 http://dx.doi.org/10.1021/ja507054j Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Shiroodi, Roohollah Kazem
Koleda, Olesja
Gevorgyan, Vladimir
1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans
title 1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans
title_full 1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans
title_fullStr 1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans
title_full_unstemmed 1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans
title_short 1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans
title_sort 1,2-boryl migration empowers regiodivergent synthesis of borylated furans
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183646/
https://www.ncbi.nlm.nih.gov/pubmed/25198147
http://dx.doi.org/10.1021/ja507054j
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AT gevorgyanvladimir 12borylmigrationempowersregiodivergentsynthesisofborylatedfurans

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