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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Bibliographic Details
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
Description
Summary: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.
ISSN:1860-5397

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