Catalytic Methylation of C--H Bonds Using CO sub(2) and H sub(2)

Formation of C--C bonds from CO sub(2) is a much sought after reaction in organic synthesis. To date, other than C--H carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about C--C bond formation. In fact, to the best of our knowledge no catalytic...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie 2014-09, Vol.126 (39), p.10644-10648
Hauptverfasser: Li, Yuehui, Yan, Tao, Junge, Kathrin, Beller, Matthias
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Formation of C--C bonds from CO sub(2) is a much sought after reaction in organic synthesis. To date, other than C--H carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about C--C bond formation. In fact, to the best of our knowledge no catalytic methylation of C--H bonds using CO sub(2) and H sub(2) has been reported. Described herein is the combination of CO sub(2) and H sub(2) for efficient methylation of carbon nucleophiles such as indoles, pyrroles, and electron-rich arenes. Comparison experiments which employ paraformaldehyde show similar reactivity for the CO sub(2)/H sub(2) system.Original Abstract: Ersatz fuer Formaldehyd: Kohlendioxid erweist sich in Gegenwart von H sub(2) als ein effizientes Methylierungsreagens fuer Kohlenstoff-Nukleophile wie 2-substituierte Indole, Pyrrole und elektronenreiche Arene. Experimentelle Daten sprechen fuer einen formalen Abfang von Formaldehyd. acac=Acetylacetonat, triphos=1,1,1-Tris(diphenylphosphanylmethyl)ethan.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201405779