Carbon Nitride-Catalyzed Photoredox Sakurai Reactions and Allylborations

Within the last couple of years, the photocatalytic, oxidative CC coupling has grown to a well‐established methodology, especially for the modification of aryl‐substituted tetrahydroisoquinoline derivatives. However, until now, this reaction is mainly restricted to the usage of strong nucleophiles...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Advanced synthesis & catalysis 2014-09, Vol.356 (13), p.2825-2829
Hauptverfasser: Möhlmann, Lennart, Blechert, Siegfried
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Within the last couple of years, the photocatalytic, oxidative CC coupling has grown to a well‐established methodology, especially for the modification of aryl‐substituted tetrahydroisoquinoline derivatives. However, until now, this reaction is mainly restricted to the usage of strong nucleophiles like nitroalkanes, cyanides, enamines, phosphonates and malonates. Within this publication we present an extension of such a method towards the application of weaker nucleophiles, namely allylstannanes, allylsilanes and allylboranes. Therefore, a very simple protocol was invented, using heterogeneous mesoporous graphitic carbon nitride (mpg‐C3N4) as catalyst and air as oxidizing agent, leading to high yields for a broad range of substrates.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400551