Chemistry is an experimental science, and the best way to enjoy it and learn about it is performing experiments.Introducing a new discovery about 657408-07-6, Name is Dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine, Computed Properties of C26H35O2P.
The Suzuki-Miyaura reaction is one of the most widely employed transformations in synthetic chemistry. Despite extensive investigation, questions remain about the mechanistic nature of the transmetalation step when catalysts based on advanced ligands such as biaryl monophosphines are used, impeding the development of improved catalysts. Here we demonstrate that the often overlooked halide salt (KX) generated as a byproduct of cross-coupling renders the transmetalation step reversible with SPhos-based catalysts, leading to severe reaction inhibition with (hetero)aryl iodides. Stoichiometric and kinetic studies reveal that halide inhibition likely originates from disfavoring the formation of a highly reactive Pd-OH intermediate. We demonstrate that changing the organic solvent in the biphasic reaction mixture from tetrahydrofuran to toluene is sufficient to minimize this inhibition and enable the general Suzuki-Miyaura coupling of (hetero)aryl iodides. Our studies suggest that halide inhibition may be a more general problem in cross-coupling reactions, especially those involving reversible transmetalation processes.
Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Computed Properties of C26H35O2P. In my other articles, you can also check out more blogs about 657408-07-6
Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate