In 2022,Krah, Sabrina; Kachel, Iris; Trapp, Oliver published an article in ChemCatChem. The title of the article was 《Electron-Rich Silicon Containing Phosphinanes for Rapid Pd-Catalyzed C-X Coupling Reactions》.Electric Literature of C5H6BNO2 The author mentioned the following in the article:
Novel silicon-containing phosphine, 4,1-phosphasilinane 2-TripC6H4P(CH2CH2)2SiMe2 (SabPhos, Trip = 2,4,6-iPr3C6H2) was prepared as a ligand for palladium-catalyzed coupling reactions. Palladium-catalyzed cross-coupling reactions are among the most useful and efficient methods for direct access to complex structures in organic synthesis. However, heteroatom-containing compounds can complicate such coupling reactions due to their competitive coordination with the palladium catalyst and electronic effects. As a result, good yields are often only obtained under harsher reaction conditions, such as high temperatures and long reaction times. Here the design of a highly active phosphine ligand is reported that provides excellent yields for C-N coupling reactions at ambient temperature Incorporation of the phosphorus atom into a cyclohexane ring maintains the pyramidal structure of the phosphorus while reducing steric hindrance. This, and a silicon atom in the cyclohexane moiety, results in an electron-rich phosphinane ligand. This novel silicon containing SabPhos ligand can be obtained in excellent yields in a straightforward synthesis. In palladium catalyzed reactions, this ligand facilitates the coupling of a broad range of heteroaryl chlorides via C-C bonds with boronic acids and C-N bonds with secondary amines in excellent yields under mild conditions. In the experiment, the researchers used 2-Pyridinylboronic acid(cas: 197958-29-5Electric Literature of C5H6BNO2)
2-Pyridinylboronic acid(cas: 197958-29-5) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. Electric Literature of C5H6BNO2