Photocatalytic Hydroalkylation of Aryl-Alkenes

[Image: see text] Here, we present a visible light-catalyzed hydroalkylation of aryl-alkenes affording C–C bonds using aryl-alkenes and alkyl iodides. We demonstrate the formation of various hydroalkylation products in excellent yields, with primary, secondary, and tertiary alkyl iodides being toler...

Descripción completa

Detalles Bibliográficos
Autores principales: Buettner, Cornelia S., Schnürch, Michael, Bica-Schröder, Katharina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9396655/
https://www.ncbi.nlm.nih.gov/pubmed/35914236
http://dx.doi.org/10.1021/acs.joc.2c01304
_version_ 1784771975338524672
author Buettner, Cornelia S.
Schnürch, Michael
Bica-Schröder, Katharina
author_facet Buettner, Cornelia S.
Schnürch, Michael
Bica-Schröder, Katharina
author_sort Buettner, Cornelia S.
collection PubMed
description [Image: see text] Here, we present a visible light-catalyzed hydroalkylation of aryl-alkenes affording C–C bonds using aryl-alkenes and alkyl iodides. We demonstrate the formation of various hydroalkylation products in excellent yields, with primary, secondary, and tertiary alkyl iodides being tolerated in the reaction. Mechanistic experiments reveal a pathway consisting of halogen atom transfer followed by a radical-polar crossover mechanism delivering the desired hydroalkylation products.
format Online
Article
Text
id pubmed-9396655
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-93966552022-08-24 Photocatalytic Hydroalkylation of Aryl-Alkenes Buettner, Cornelia S. Schnürch, Michael Bica-Schröder, Katharina J Org Chem [Image: see text] Here, we present a visible light-catalyzed hydroalkylation of aryl-alkenes affording C–C bonds using aryl-alkenes and alkyl iodides. We demonstrate the formation of various hydroalkylation products in excellent yields, with primary, secondary, and tertiary alkyl iodides being tolerated in the reaction. Mechanistic experiments reveal a pathway consisting of halogen atom transfer followed by a radical-polar crossover mechanism delivering the desired hydroalkylation products. American Chemical Society 2022-08-01 2022-08-19 /pmc/articles/PMC9396655/ /pubmed/35914236 http://dx.doi.org/10.1021/acs.joc.2c01304 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Buettner, Cornelia S.
Schnürch, Michael
Bica-Schröder, Katharina
Photocatalytic Hydroalkylation of Aryl-Alkenes
title Photocatalytic Hydroalkylation of Aryl-Alkenes
title_full Photocatalytic Hydroalkylation of Aryl-Alkenes
title_fullStr Photocatalytic Hydroalkylation of Aryl-Alkenes
title_full_unstemmed Photocatalytic Hydroalkylation of Aryl-Alkenes
title_short Photocatalytic Hydroalkylation of Aryl-Alkenes
title_sort photocatalytic hydroalkylation of aryl-alkenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9396655/
https://www.ncbi.nlm.nih.gov/pubmed/35914236
http://dx.doi.org/10.1021/acs.joc.2c01304
work_keys_str_mv AT buettnercornelias photocatalytichydroalkylationofarylalkenes
AT schnurchmichael photocatalytichydroalkylationofarylalkenes
AT bicaschroderkatharina photocatalytichydroalkylationofarylalkenes

Ejemplares similares