Rapid palladium-catalyzed aminations of aryl chlorides with aliphatic amines under temperature-controlled microwave heating

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

“…[223] Maes et al have shown that temperature-controlled microwave heating allows the reaction time of palladium-catalyzed aryl chloride amination reactions with dialkylbiaryl phosphane ligands to be reduced to just 10 minutes, with yields comparable to those obtained with conventional heating (Scheme 60). [224,225] The same authors were later able to increase the scale of these reactions in an appropriate microwave reactor. [226] A modified version of these conditions was subsequently employed in an intramolecular reaction by Rozman and coworkers in the synthesis of chlorinated phenothiazines as models for dioxin-like compounds (Scheme 61).…”

Biarylphosphanliganden in der palladiumkatalysierten Aminierung

“…Die Ausbeuten sind vergleichbar mit denen von Reaktionen unter herkömmlichem Erhitzen (Schema 60). [224,225] Mithilfe eines geeigneten Mikrowellenreaktors gelang es denselben Autoren später, diese Reaktionen in größerem Maßstab auszuführen. [226] Nachfolgend modifizierten Rozman und Mitarbeiter diese Bedingungen bei einer intramolekularen Reaktion zur Synthese von chlorierten Phenothiazinen, die als Modell für Dioxine dienten (Schema 61).…”

Microwave‐Heated Transition Metal‐Catalyzed Coupling Reactions

“…To address this problem, Caddick and co-workers investigated the outcome of palladium-N-heterocyclic carbenes as catalysts in rapid microwave-promoted reactions [169]. p-Tolyl and -anisyl chloride were coupled with aromatic and aliphatic amines in generally good yields within 6 min at 160 • C. Reactions between tolyl/anisyl/phenyl chlorides and aliphatic amines were also reported by Maes et al using a more classical reaction system with a phosphine ligand and a strong base, affording the desired products after 10 min of heating at 110-200 • C [170].…”