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Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis
Science  (IF47.728),  Pub Date : 2021-10-15, DOI: 10.1126/science.abj4213
Samuel H. Newman-Stonebraker, Sleight R. Smith, Julia E. Borowski, Ellyn Peters, Tobias Gensch, Heather C. Johnson, Matthew S. Sigman, Abigail G. Doyle

Chemists often use statistical analysis of reaction data with molecular descriptors to identify structure-reactivity relationships, which can enable prediction and mechanistic understanding. In this study, we developed a broadly applicable and quantitative classification workflow that identifies reactivity cliffs in 11 Ni- and Pd-catalyzed cross-coupling datasets using monodentate phosphine ligands. A distinctive ligand steric descriptor, minimum percent buried volume [%Vbur (min)], is found to divide these datasets into active and inactive regions at a similar threshold value. Organometallic studies demonstrate that this threshold corresponds to the binary outcome of bisligated versus monoligated metal and that %Vbur (min) is a physically meaningful and predictive representation of ligand structure in catalysis.