Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts

A ruthenium-catalyzed photoredox coupling of substituted N-aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. Furthermore, secondary alkyl and allyl groups were also successfully introduced via the same me...

Descripción completa

Detalles Bibliográficos
Autores principales: Schönbauer, David, Sambiagio, Carlo, Noël, Timothy, Schnürch, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7189001/
https://www.ncbi.nlm.nih.gov/pubmed/32395184
http://dx.doi.org/10.3762/bjoc.16.74
_version_ 1783527415893458944
author Schönbauer, David
Sambiagio, Carlo
Noël, Timothy
Schnürch, Michael
author_facet Schönbauer, David
Sambiagio, Carlo
Noël, Timothy
Schnürch, Michael
author_sort Schönbauer, David
collection PubMed
description A ruthenium-catalyzed photoredox coupling of substituted N-aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. Furthermore, secondary alkyl and allyl groups were also successfully introduced via the same method. Additionally, the typically applied N-phenyl group in the THIQ substrate could be replaced by the cleavable p-methoxyphenyl (PMP) group and successful N-deprotection was demonstrated.
format Online
Article
Text
id pubmed-7189001
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-71890012020-05-11 Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts Schönbauer, David Sambiagio, Carlo Noël, Timothy Schnürch, Michael Beilstein J Org Chem Full Research Paper A ruthenium-catalyzed photoredox coupling of substituted N-aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. Furthermore, secondary alkyl and allyl groups were also successfully introduced via the same method. Additionally, the typically applied N-phenyl group in the THIQ substrate could be replaced by the cleavable p-methoxyphenyl (PMP) group and successful N-deprotection was demonstrated. Beilstein-Institut 2020-04-21 /pmc/articles/PMC7189001/ /pubmed/32395184 http://dx.doi.org/10.3762/bjoc.16.74 Text en Copyright © 2020, Schönbauer et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Schönbauer, David
Sambiagio, Carlo
Noël, Timothy
Schnürch, Michael
Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
title Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
title_full Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
title_fullStr Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
title_full_unstemmed Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
title_short Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
title_sort photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with n-alkylpyrydinium salts
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7189001/
https://www.ncbi.nlm.nih.gov/pubmed/32395184
http://dx.doi.org/10.3762/bjoc.16.74
work_keys_str_mv AT schonbauerdavid photocatalyticdeaminativebenzylationandalkylationoftetrahydroisoquinolineswithnalkylpyrydiniumsalts
AT sambiagiocarlo photocatalyticdeaminativebenzylationandalkylationoftetrahydroisoquinolineswithnalkylpyrydiniumsalts
AT noeltimothy photocatalyticdeaminativebenzylationandalkylationoftetrahydroisoquinolineswithnalkylpyrydiniumsalts
AT schnurchmichael photocatalyticdeaminativebenzylationandalkylationoftetrahydroisoquinolineswithnalkylpyrydiniumsalts

Ejemplares similares