Recent Progress in Nickel‐Catalyzed Biaryl Coupling

Abstract

Nickel catalysis for biaryl coupling reactions has received significant attention as a less expensive and less toxic alternative to “standard” palladium catalysis. Here we describe recent developments in nickel‐catalyzed biaryl coupling methodology, along with mechanistic studies and applications. In particular we focus on nickel‐catalyzed coupling reactions in which “unreactive” bonds such as C–H, C–O, and C–C bonds are converted into biaryl moieties.

Recent advances in the application of group-10 transition metal based catalysts in C–H activation and functionalization

“…Among those, Ni-based catalysts have attracted attention due to their low toxicity and low cost in comparison to other catalytic systems [16]. Ni also has a high potential for C−H bond activation in isolated model systems, in the gas phase, and is less expensive in comparison to 4d-and 5d-elements, though the latter are more reactive [16,17]. Ni-based catalysts have been used for the synthesis of biologically active agents such as febuxostat, tafamidid and texaline.…”

Katalytische Funktionalisierung von C(sp2)‐H‐ und C(sp3)‐H‐Bindungen unter Verwendung von zweizähnigen dirigierenden Gruppen

“…[52] Nach dem ersten Bericht von Kleimann und Dubeck über die gezielte Insertion von Nickel in eine C-H-Bindung [7] sind lange Zeit keine Beispiele nickelkatalysierter Umwandlungen von ortho-C-H-Bindungen mittels einer dirigierenden Gruppe beschrieben worden. Erst Chatani et al berichteten über die erste nickelkatalysierte Umwandlung von ortho-C-H-Bindungen unter Verwendung einer dirigierenden Gruppe.…”

A macrocyclic Pd(II)–Ni(II) complex in Heck and Suzuki reactions

“…In some cases the nickel based catalysts even surpass palladium catalysts in cross-coupling reactions [35,36]. In a recent communication a very interesting effect of cooperative catalysis by palladium-nickel binary nanocluster in Suzuki-Miyaura reaction has been reported [37].…”