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

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

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)
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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 languageEnglish
Pages (from-to)809-817
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume16
DOIs
Publication statusPublished - 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.

Keywords

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

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