Daw, Prosenjit published the artcileBifunctional Water Activation for Catalytic Hydration of Organonitriles, Application In Synthesis of 16332-06-2, the publication is Organometallics (2012), 31(9), 3790-3797, database is CAplus.
Treatment of [Rh(COD)(μ-Cl)]2 with excess tBuOK and subsequent addition of 2 equiv of PIN·HBr in THF afforded [Rh(COD)(κC2-PIN)Br] (1) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene, COD = 1,5-cyclooctadiene). The x-ray structure of 1 confirms ligand coordination to Rh(COD)Br through the carbene C featuring an unbound naphthyridine. Compound 1 is an excellent catalyst for the hydration of a wide variety of organonitriles at ambient temperature, providing the corresponding organoamides. In general, smaller substrates gave higher yields compared with sterically bulky nitriles. A turnover frequency of 20,000 h-1 was achieved for the acrylonitrile. A similar Rh(I) catalyst without the naphthyridine appendage turned out to be inactive. DFT studies are undertaken to gain insight on the hydration mechanism. A 1:1 catalyst-H2O adduct was identified, which indicates that the naphthyridine group steers the catalytically relevant H2O mol. to the active metal site via double H-bonding interactions, providing significant entropic advantage to the hydration process. The calculated transition state (TS) reveals multicomponent cooperativity involving proton movement from the H2O to the naphthyridine N and a complementary interaction between the hydroxide and the nitrile C. Bifunctional H2O activation and cooperative proton migration are recognized as the key steps in the catalytic cycle.
Organometallics published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Application In Synthesis of 16332-06-2.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem