Gallou, Fabrice (2020) N2Phos. An easily made, highly effective ligand designed for ppm level Pd-catalyzed Suzuki-Miyaura cross couplings in water. Chemical science, 11. pp. 5205-5212.

Abstract

A new biaryl phosphine-containing ligand from an active palladium catalyst for ppm level Suzuki-Miyaura couplings, enabled by an aqueous micellar reaction medium. A wide array of functionalized substrates including aryl/hetroaryl bromides is amenable, as are, notably, chlorides. The catalytic system is both general and highly effective at low palladium loadings (1000-2500 ppm or 0.10-0.25 mol %). Density funtional theory calculations suggest that greater steric congestion in N2Phos induces increased steric crowding around the Pd center, preventing formation of a 2:1 ligand-Pd complex found with EvanPhos (and less bulky ligands) that could slow oxidative addition to aryl chlorides.

Item Type:	Article
Date Deposited:	14 Jul 2020 00:45
Last Modified:	14 Jul 2020 00:45
URI:	https://oak.novartis.com/id/eprint/42254