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

David Schönbauer; Carlo Sambiagio; Timothy Noël; Michael Schnürch

doi:10.3762/bjoc.16.74

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

David Schönbauer, Carlo Sambiagio, Timothy Noël, Michael Schnürch (Corresponding author)

Micro Flow Chemistry and Synthetic Methodology

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Abstract

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.

Original language	English
Pages (from-to)	809-817
Number of pages	9
Journal	Beilstein Journal of Organic Chemistry
Volume	16
DOIs	https://doi.org/10.3762/bjoc.16.74
Publication status	Published - 21 Apr 2020

Bibliographical note

This article is part of the thematic issue "Advances in photoredox catalysis" and is dedicated to Professor Marko D. Mihovilovic on the occasion of his 50th birthday.

Funding

D.S. acknowledges CHAOS COST Action CA15106 for financial support of a STSM at Eindhoven University of Technology. C.S. acknowledges the European Union for a Marie Curie European Fellowship (FlowAct, Grant No.794072)

Funders	Funder number
Horizon 2020 Framework Programme	794072
European Commission
Eindhoven University of Technology

Keywords

C(sp)–C(sp) coupling
C–H functionalization
Deaminative coupling
Katritzky salt
Photoredox catalysis

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10.3762/bjoc.16.74

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Cite this

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title = "Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts",

abstract = "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.",

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AU - Sambiagio, Carlo

AU - Noël, Timothy

AU - Schnürch, Michael

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N2 - 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.

AB - 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.

KW - C(sp)–C(sp) coupling

KW - C–H functionalization

KW - Deaminative coupling

KW - Katritzky salt

KW - Photoredox catalysis

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JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Bibliographical note

Funding

Keywords

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