Suzuki–Miyaura Coupling Reaction by Pd^II‐Catalyzed Aromatic CH Bond Activation Directed by an N‐Alkyl Acetamino Group

Abstract

A seamless join: An efficient method to construct a C(sp2)C(sp2) bond has been developed by using a Suzuki–Miyaura‐type coupling of N‐alkyl acetanilides with boronic acids. The reaction was catalyzed by a PdII species and the CH bond activation was directed by the acetamino group (see scheme). This reaction offers a halogen‐free method to construct complicated structures.

Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions

“…36). 87 A number of commercially available boronic acids proved effective as arylating reagents, particularly those containing electron-donating groups. In contrast, the presence of electron withdrawing substituents or ortho -substitution on the boronic acid resulted in lower yields.…”

Palladium(II)‐katalysierte C‐H‐Aktivierung/C‐C‐Kreuzkupplung: Vielseitigkeit und Anwendbarkeit

“…[64] werden können (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30) [65] Diese hochreaktiven Anilidsubstrate können auch in orthoPosition mit Arylboronsäuren gekuppelt werden. [66] Wie bereits in Abschnitt 2 erläutert wurde, schlugen de Vries et al in einer frühen Untersuchung vor, [13] dass die Reaktion dieses Anilids mit Pd(OAc) 2 über eine elektrophile Palladierung verläuft.…”

Recent Advances in Direct Arylation via Palladium-Catalyzed Aromatic C-H Activation

“…42 In this transformation, acetanilides, Nacetyltetrahydroquinolines and N-acetylindolines are all good substrates. Different functionalities, regardless of where they are located on the substrate or the arylboronic acid, are compatible with this transformation.…”