Yasuda, Hiroyuki published the artcileEffects of bulky ligands and water in Pd-catalyzed oxidative carbonylation of phenol, Synthetic Route of 138429-17-1, the publication is Journal of Molecular Catalysis A: Chemical (2005), 236(1-2), 149-155, database is CAplus.
A diaryloxy Pd complex with a bulky 6,6′-dimethyl-2,2′-bipyridyl (6,6′-Me2bpy) ligand reacted with pressurized CO (5 MPa) at 25 °C to produce a diaryl carbonate, whereas a diaryloxy Pd complex with an unsubstituted 2,2′-bipyridyl (bpy) ligand hardly reacted. 1H and 13C NMR studies revealed that CO inserts into one of the Pd-O bonds in the latter complex to form a Pd aryloxycarbonyl complex, but that the subsequent reductive elimination of diaryl carbonate is slow. This is consistent with the much higher catalytic activity of the Pd-(6,6′-Me2bpy) system for the oxidative carbonylation of phenol compared to the Pd-bpy system. To verify the steric effects of the ligands, the catalytic performance was also examined using 2,2′-bioxazolyl ligands with various substituents. Introducing bulky substituents at the 4,4′-position effectively promoted the catalytic reaction. The TONs of DPC increased in the following order: Me < benzyl < iso-Bu < tert-Bu. The methylene-bridged bioxazolyl ligand with tert-Bu groups gave the highest TON (54 mol-DPC/mol-Pd in 3 h), which is higher than the TON for the 6,6′-Me2bpy ligand. The addition of mol. sieve 3A to the reaction system further improved the TON and suppressed Ph salicylate formation. The addition of the mol. sieve also prevented CO2 formation, probably due to suppression of the reaction between CO and water, in addition to suppression of the hydrolysis of DPC.
Journal of Molecular Catalysis A: Chemical published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C7H16ClNO2, Synthetic Route of 138429-17-1.
Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem