N‐methyliminodiacetic acid as a simple and highly efficient ligand for palladium‐catalyzed Suzuki–Miyaura cross‐coupling of aryl chlorides

Abstract

A simple, air-stable, inexpensive and easily prepared molecule, N-methyliminodiacetic acid (MIDA), is reported as a ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of phenylboronic acid with aryl chlorides. The yield of the corresponding Suzuki coupling reaction is up to around 90% at both high temperature of 80°C and room temperature under ambient atmosphere.

Air-Stable [(R3P)PdCl2]2Complexes of Neopentylphosphines as Cross-Coupling Precatalysts: Catalytic Application and Mechanism of Catalyst Activation and Deactivation

“…Palladium-catalyzed cross-couplings, such as the Suzuki coupling, are typically run under an inert atmosphere to protect the Pd(0) catalytic intermediate, as well as air-sensitive ligands. Catalysts derived from air-stable ligands, as well as strongly bound NHC ligands, have been shown to perform Suzuki coupling in an air atmosphere . Electron-rich trialkylphosphine-based systems generally are not tolerant of air, however.…”

Si-thiol supported atomic-scale palladium as efficient and recyclable catalyst for Suzuki coupling reaction

“…The Pd-catalyzed Suzuki coupling reactions have been widely used in modern synthesis [1]. However, the use of Pd in active pharmaceutical ingredients (APIs) could result in the possibility of Pd-containing impurities in the isolated products, and the post reaction removal of Pd is a challenging task [2]. To meet strict limits for heavy metal residues in APIs, adsorption of the residual Pd to an appropriate solid scaffold followed by the removal of the absorbent with Pd by filtration from the process stream.…”