Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes

[Image: see text] Radical α-C-H functionalization of alk-5-enyl boronic esters with concomitant functionalization of the alkene moiety is reported. These cascades comprise perfluoroalkyl radical addition to the alkene moiety of a boronate complex, intramolecular hydrogen atom transfer (HAT), single...

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Autores principales: Wang, Dinghai, Jana, Kalipada, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8353630/
https://www.ncbi.nlm.nih.gov/pubmed/34260254
http://dx.doi.org/10.1021/acs.orglett.1c01998
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author Wang, Dinghai
Jana, Kalipada
Studer, Armido
author_facet Wang, Dinghai
Jana, Kalipada
Studer, Armido
author_sort Wang, Dinghai
collection PubMed
description [Image: see text] Radical α-C-H functionalization of alk-5-enyl boronic esters with concomitant functionalization of the alkene moiety is reported. These cascades comprise perfluoroalkyl radical addition to the alkene moiety of a boronate complex, intramolecular hydrogen atom transfer (HAT), single electron oxidation, and 1,2-alkyl/aryl migration. The boronate complexes are readily generated in situ by reaction of the alkenyl boronic esters with alkyl or aryl lithium reagents. Products are formed in a divergent approach by varying carbon radical precursors as well as alkyl/aryl lithium donors, and reactions proceed under mild conditions upon UV irradiation.
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spelling pubmed-83536302021-08-10 Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes Wang, Dinghai Jana, Kalipada Studer, Armido Org Lett [Image: see text] Radical α-C-H functionalization of alk-5-enyl boronic esters with concomitant functionalization of the alkene moiety is reported. These cascades comprise perfluoroalkyl radical addition to the alkene moiety of a boronate complex, intramolecular hydrogen atom transfer (HAT), single electron oxidation, and 1,2-alkyl/aryl migration. The boronate complexes are readily generated in situ by reaction of the alkenyl boronic esters with alkyl or aryl lithium reagents. Products are formed in a divergent approach by varying carbon radical precursors as well as alkyl/aryl lithium donors, and reactions proceed under mild conditions upon UV irradiation. American Chemical Society 2021-07-14 2021-08-06 /pmc/articles/PMC8353630/ /pubmed/34260254 http://dx.doi.org/10.1021/acs.orglett.1c01998 Text en © 2021 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 Wang, Dinghai
Jana, Kalipada
Studer, Armido
Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes
title Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes
title_full Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes
title_fullStr Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes
title_full_unstemmed Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes
title_short Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes
title_sort intramolecular hydrogen atom transfer induced 1,2-migration of boronate complexes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8353630/
https://www.ncbi.nlm.nih.gov/pubmed/34260254
http://dx.doi.org/10.1021/acs.orglett.1c01998
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AT janakalipada intramolecularhydrogenatomtransferinduced12migrationofboronatecomplexes
AT studerarmido intramolecularhydrogenatomtransferinduced12migrationofboronatecomplexes

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