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Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration

[Image: see text] A catalyst-free oxyboration reaction of alkynes is developed. The resulting borylated isocoumarins and 2-pyrones are isolated as boronic acids, pinacolboronate esters, or potassium organotrifluoroborate salts, providing a variety of bench-stable organoboron building blocks for down...

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Autores principales: Faizi, Darius J., Issaian, Adena, Davis, Ashlee J., Blum, Suzanne A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4768685/
https://www.ncbi.nlm.nih.gov/pubmed/26849770
http://dx.doi.org/10.1021/jacs.5b12989
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author Faizi, Darius J.
Issaian, Adena
Davis, Ashlee J.
Blum, Suzanne A.
author_facet Faizi, Darius J.
Issaian, Adena
Davis, Ashlee J.
Blum, Suzanne A.
author_sort Faizi, Darius J.
collection PubMed
description [Image: see text] A catalyst-free oxyboration reaction of alkynes is developed. The resulting borylated isocoumarins and 2-pyrones are isolated as boronic acids, pinacolboronate esters, or potassium organotrifluoroborate salts, providing a variety of bench-stable organoboron building blocks for downstream functionalization. This method has functional group compatibility, is scalable, and proceeds with readily available materials: B-chlorocatecholborane and methyl esters. Mechanistic studies indicate that the B-chlorocatecholborane acts as a carbophilic Lewis acid toward the alkyne, providing a mechanistically distinct pathway for oxyboration that avoids B–O σ bond formation and enables this catalyst-free route.
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spelling pubmed-47686852017-02-05 Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration Faizi, Darius J. Issaian, Adena Davis, Ashlee J. Blum, Suzanne A. J Am Chem Soc [Image: see text] A catalyst-free oxyboration reaction of alkynes is developed. The resulting borylated isocoumarins and 2-pyrones are isolated as boronic acids, pinacolboronate esters, or potassium organotrifluoroborate salts, providing a variety of bench-stable organoboron building blocks for downstream functionalization. This method has functional group compatibility, is scalable, and proceeds with readily available materials: B-chlorocatecholborane and methyl esters. Mechanistic studies indicate that the B-chlorocatecholborane acts as a carbophilic Lewis acid toward the alkyne, providing a mechanistically distinct pathway for oxyboration that avoids B–O σ bond formation and enables this catalyst-free route. American Chemical Society 2016-02-05 2016-02-24 /pmc/articles/PMC4768685/ /pubmed/26849770 http://dx.doi.org/10.1021/jacs.5b12989 Text en Copyright © 2016 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 Faizi, Darius J.
Issaian, Adena
Davis, Ashlee J.
Blum, Suzanne A.
Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration
title Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration
title_full Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration
title_fullStr Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration
title_full_unstemmed Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration
title_short Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration
title_sort catalyst-free synthesis of borylated lactones from esters via electrophilic oxyboration
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4768685/
https://www.ncbi.nlm.nih.gov/pubmed/26849770
http://dx.doi.org/10.1021/jacs.5b12989
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