Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation

[Image: see text] A rapid synthesis of aminoboranes from amine-boranes utilizing an iodination/dehydroiodination sequence is described. Monomeric aminoboranes are generated exclusively from several substrate adducts, following an E2-type elimination, with the added base playing a critical role in mo...

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Autores principales: Ramachandran, P. Veeraraghavan, Hamann, Henry J., Mishra, Sukriti
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9089688/
https://www.ncbi.nlm.nih.gov/pubmed/35573212
http://dx.doi.org/10.1021/acsomega.2c01461
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author Ramachandran, P. Veeraraghavan
Hamann, Henry J.
Mishra, Sukriti
author_facet Ramachandran, P. Veeraraghavan
Hamann, Henry J.
Mishra, Sukriti
author_sort Ramachandran, P. Veeraraghavan
collection PubMed
description [Image: see text] A rapid synthesis of aminoboranes from amine-boranes utilizing an iodination/dehydroiodination sequence is described. Monomeric aminoboranes are generated exclusively from several substrate adducts, following an E2-type elimination, with the added base playing a critical role in monomer vs dimer formation. Diisopropylaminoborane formed using this methodology has been applied to a one-pot palladium-catalyzed conversion of iodo- and bromoarenes to the corresponding boronates. Additionally, modification of the workup allows for isolation of the boronic acid and recovery of the utilized amine.
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spelling pubmed-90896882022-05-12 Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation Ramachandran, P. Veeraraghavan Hamann, Henry J. Mishra, Sukriti ACS Omega [Image: see text] A rapid synthesis of aminoboranes from amine-boranes utilizing an iodination/dehydroiodination sequence is described. Monomeric aminoboranes are generated exclusively from several substrate adducts, following an E2-type elimination, with the added base playing a critical role in monomer vs dimer formation. Diisopropylaminoborane formed using this methodology has been applied to a one-pot palladium-catalyzed conversion of iodo- and bromoarenes to the corresponding boronates. Additionally, modification of the workup allows for isolation of the boronic acid and recovery of the utilized amine. American Chemical Society 2022-04-14 /pmc/articles/PMC9089688/ /pubmed/35573212 http://dx.doi.org/10.1021/acsomega.2c01461 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Ramachandran, P. Veeraraghavan
Hamann, Henry J.
Mishra, Sukriti
Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation
title Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation
title_full Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation
title_fullStr Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation
title_full_unstemmed Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation
title_short Aminoboranes via Tandem Iodination/Dehydroiodination for One-Pot Borylation
title_sort aminoboranes via tandem iodination/dehydroiodination for one-pot borylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9089688/
https://www.ncbi.nlm.nih.gov/pubmed/35573212
http://dx.doi.org/10.1021/acsomega.2c01461
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AT mishrasukriti aminoboranesviatandemiodinationdehydroiodinationforonepotborylation

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