Cargando…

Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades

[Image: see text] Radical 1,3-carboheteroarylation and 1,3-hydroalkylation of allylboronic esters comprising a 1,2-boron shift is reported. Allylboronic esters are generally used in synthesis as allylation reagents, where the boronic ester moiety gets lost. In the introduced cascades, alkylboronic e...

Descripción completa

Detalles Bibliográficos
Autores principales: Jana, Kalipada, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8822490/
https://www.ncbi.nlm.nih.gov/pubmed/35080407
http://dx.doi.org/10.1021/acs.orglett.2c00039
_version_ 1784646618168950784
author Jana, Kalipada
Studer, Armido
author_facet Jana, Kalipada
Studer, Armido
author_sort Jana, Kalipada
collection PubMed
description [Image: see text] Radical 1,3-carboheteroarylation and 1,3-hydroalkylation of allylboronic esters comprising a 1,2-boron shift is reported. Allylboronic esters are generally used in synthesis as allylation reagents, where the boronic ester moiety gets lost. In the introduced cascades, alkylboronic esters are obtained with the boron entity remaining in the product. The carboheteroarylation of the allylboronic esters are conducted without a metal catalyst, and the 1,3-hydroalkylation is achieved using iron catalysis. Both reactions work efficiently under mild conditions.
format Online
Article
Text
id pubmed-8822490
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-88224902022-02-08 Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades Jana, Kalipada Studer, Armido Org Lett [Image: see text] Radical 1,3-carboheteroarylation and 1,3-hydroalkylation of allylboronic esters comprising a 1,2-boron shift is reported. Allylboronic esters are generally used in synthesis as allylation reagents, where the boronic ester moiety gets lost. In the introduced cascades, alkylboronic esters are obtained with the boron entity remaining in the product. The carboheteroarylation of the allylboronic esters are conducted without a metal catalyst, and the 1,3-hydroalkylation is achieved using iron catalysis. Both reactions work efficiently under mild conditions. American Chemical Society 2022-01-26 2022-02-04 /pmc/articles/PMC8822490/ /pubmed/35080407 http://dx.doi.org/10.1021/acs.orglett.2c00039 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 Jana, Kalipada
Studer, Armido
Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades
title Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades
title_full Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades
title_fullStr Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades
title_full_unstemmed Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades
title_short Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades
title_sort allylboronic esters as acceptors in radical addition, boron 1,2-migration, and trapping cascades
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8822490/
https://www.ncbi.nlm.nih.gov/pubmed/35080407
http://dx.doi.org/10.1021/acs.orglett.2c00039
work_keys_str_mv AT janakalipada allylboronicestersasacceptorsinradicaladditionboron12migrationandtrappingcascades
AT studerarmido allylboronicestersasacceptorsinradicaladditionboron12migrationandtrappingcascades