Base and Cation Effects on the Suzuki Cross-Coupling of Bulky Arylboronic Acid with Halopyridines: Synthesis of Pyridylphenols

Abstract

Strong base and large size cation have been shown to accelerate the rate and the yield of Suzuki coupling of a sterically bulky boronic acid with halopyridines in DME for the synthesis of pyridylphenols.

Harnessing Cascade Suzuki‐Cyclization Reactions of Pyrazolo[3,4‐b]pyridine for the Synthesis of Tetracyclic Fused Heteroaromatics

“…The Gronowitz conditions, which were successful with electron‐deficient chloropyridines[22a], [22b] and with hindered boronic acids were also tested (Table , entry 5), but this gave dehalogenated compound 5 (86 %) as the sole product. With the aim of carrying out a mild and phosphine‐free Suzuki reaction, bis(dicyclohexylamine)palladium diacetate (DAPCy) was tested as a catalyst, and gave excellent yields (Table , entry 6).…”

Bulky N-acyl-pyridylbenzamidine Ligands for Palladium Catalyzed Suzuki–Miyaura Reaction

“…It indicated that ligands with stronger electron-donating substituents rendered a promotion of the oxidative addition process and stabilized the palladium complexes. What's more, bulky hindrance on ligands could further facilitate the reductive elimination in the catalytic cycle [33,34]. Therefore, L4 was applied in the following palladium catalyzed Suzuki-Miyaura reactions.…”

Crossing the Borders Between Homogeneous and Heterogeneous Catalysis: Developing Recoverable and Reusable Catalytic Systems

“…Weaker or stronger basicity leads to a decrease on the overall catalytic activity. In a certain way, this resembles the studies in solution where it has been found that the strength of the base plays an important role [97][98][99][100][101][102][103]. Apparently, palladium(0) is increasingly reluctant to undergo re-oxidation to palladium(II) if the basic sites are too strong.…”