Multi-arylated phosphine ligands are ubiquitous is modern palladium catalyzed cross-coupling applications with biarylphosphines featuring the most often. While many of the best performing palladium catalysts known to date contain biarylphoshpines, new insights into the mechanism of these systems indicate that greater performance is achievable by moving to from a biaryl to a teraryl ligand backbone. This work will highlight the development of the multi-arylated phosphine ligand evolution. Both empirical and computational evidence will be presented to rationalize the tangible catalytic enhancement. Additionally, the insight can be utilized to facilitate catalyst selection and leveraged to develop an unprecedented, one-pot, triple cross-coupling sequence of borylation, Suzuki, and amination to afford functionalized molecules with high overall yield.

Mechanistic insights and new applications of palladium catalysts with multi-arylated phosphine ligands for cross-coupling

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.