Effects of Multiple Catalyst Deactivation Pathways and Continuous Ligand Recycling on the Kinetics of Pd-Catalyzed
Neil A Strotman1, Maxime C Soumeillant1, Keming Zhu1
1Chemical and Synthetic Development , Bristol-Myers Squibb , 1 Squibb Drive , New Brunswick , New Jersey 08903 , United States.
Abstract:
Unusual Pd deactivation and inhibition pathways were observed in a C-N coupling system. Irreversible catalyst deactivation involved C-H insertion of Pd into BippyPhos leading to an off-cycle palladaphosphacyclobutene. Product inhibition led to deactivated Pd but released ligand in the process, allowing it to react with additional Pd precursor to re-enter the catalytic cycle. In situ recycling of the ligand allowed for an input L/Pd ratio of ≪1 with no impact on reaction kinetics.
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