Development of an Aryl Amination Catalyst with Broad Scope Guided by Consideration of Catalyst Stability.

ABSTRACT: We have developed a new dialkylbiaryl monophosphine ligand, GPhos, that supports a palladium catalyst capable of promoting carbon-nitrogen cross-coupling reactions between a variety of primary amines and aryl halides; in many cases, these reactions can be carried out at room temperature. The reaction development was guided by the idea that the productivity of catalysts employing BrettPhos-like ligands is limited by their lack of stability at room temperature. Specifically, it was hypothesized that primary amine and N-heteroaromatic substrates can displace the phosphine ligand, leading to the formation of catalytically dormant palladium complexes that reactivate only upon heating. This notion was supported by the synthesis and kinetic study of a putative off-cycle Pd complex. Consideration

SUBMITTER: McCann SD 

PROVIDER: S-EPMC8057821 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature