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

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...

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Main Authors: David Schönbauer, Carlo Sambiagio, Timothy Noël, Michael Schnürch
Format: Article
Language:English
Published: Beilstein-Institut 2020-04-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
c–h functionalization
c(sp3)–c(sp3) coupling
deaminative coupling
katritzky salt
photoredox catalysis
Online Access:https://doi.org/10.3762/bjoc.16.74
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spelling doaj-75d088305d19408caca332446314c71e2021-04-02T14:08:44ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-04-0116180981710.3762/bjoc.16.741860-5397-16-74Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium saltsDavid Schönbauer0Carlo Sambiagio1Timothy Noël2Michael Schnürch3Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060 Vienna, AustriaDepartment of Chemical Engineering and Chemistry, Micro Flow Chemistry and Synthetic Methodology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The NetherlandsDepartment of Chemical Engineering and Chemistry, Micro Flow Chemistry and Synthetic Methodology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ Eindhoven, The NetherlandsInstitute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060 Vienna, AustriaA 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.https://doi.org/10.3762/bjoc.16.74c–h functionalizationc(sp3)–c(sp3) couplingdeaminative couplingkatritzky saltphotoredox catalysis
collection DOAJ
language English
format Article
sources DOAJ
author David Schönbauer
Carlo Sambiagio
Timothy Noël
Michael Schnürch
spellingShingle David Schönbauer
Carlo Sambiagio
Timothy Noël
Michael Schnürch
Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
Beilstein Journal of Organic Chemistry
c–h functionalization
c(sp3)–c(sp3) coupling
deaminative coupling
katritzky salt
photoredox catalysis
author_facet David Schönbauer
Carlo Sambiagio
Timothy Noël
Michael Schnürch
author_sort David Schönbauer
title 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_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_sort photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with n-alkylpyrydinium salts
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2020-04-01
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.
topic c–h functionalization
c(sp3)–c(sp3) coupling
deaminative coupling
katritzky salt
photoredox catalysis
url https://doi.org/10.3762/bjoc.16.74
work_keys_str_mv AT davidschonbauer photocatalyticdeaminativebenzylationandalkylationoftetrahydroisoquinolineswithnalkylpyrydiniumsalts
AT carlosambiagio photocatalyticdeaminativebenzylationandalkylationoftetrahydroisoquinolineswithnalkylpyrydiniumsalts
AT timothynoel photocatalyticdeaminativebenzylationandalkylationoftetrahydroisoquinolineswithnalkylpyrydiniumsalts
AT michaelschnurch photocatalyticdeaminativebenzylationandalkylationoftetrahydroisoquinolineswithnalkylpyrydiniumsalts
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