The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide( cas:313342-24-4 ) is researched.Recommanded Product: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide.Dub, Pavel A.; Wang, Hui; Matsunami, Asuka; Gridnev, Ilya D.; Kuwata, Shigeki; Ikariya, Takao published the article 《C-F bond breaking through aromatic nucleophilic substitution with a hydroxo ligand mediated via water bifunctional activation》 about this compound( cas:313342-24-4 ) in Bulletin of the Chemical Society of Japan. Keywords: cyclometalated oxobenzenesulfonyldiamido ruthenium complex preparation crystal structure DFT; crystal structure cyclometalated oxobenzenesulfonyldiamido ruthenium iridium complex; mol structure cyclometalated oxobenzenesulfonyldiamido ruthenium iridium complex; hydration reaction benzenesulfonyldiamido ruthenium iridium complex DFT; optimized geometry cyclometalated oxobenzenesulfonyldiamido ruthenium iridium complex DFT. Let’s learn more about this compound (cas:313342-24-4).
Transformation of C-F to C-O bond mediated by bifunctional Ru and Ir complexes is described. This reaction proceeds through water O-H bond cleavage via metal-ligand cooperation in the newly developed 16e bifunctional Ru and Ir complexes bearing chiral (S,S)-C6F5SO2-dpen ligand. The 16e Ru amido complex, [Ru{(S,S)-Pfbsdpen}(η6-hmb)] (1a), readily reacted with H2O at room temperature producing oxometallacyclic compound, (R)-[Ru{κ3(N,N’,O)-(S,S)-OC6F4SO2dpen}(η6-hmb)] (3aR), as a result of bifunctional H2O activation followed by ortho-oxometalation via SNAr. Complex 3aR can be prepared either from 1a or, more conveniently from its 18e chlorido precursor, complex (R)-[RuCl{(S,S)-Pfbsdpen}(η6-hmb)]. On the contrary, the 16e Ir amido complex, [Cp*Ir{(S,S)-Pfbsdpen}] (2), is kinetically stable toward H2O at room temperature Oxometallacyclic compound (R)-[Cp*Ir{κ3(N,N’,O)-(S,S)-OC6F4SO2dpen}] (4R) was prepared in high yield by the reaction of [Cp*IrCl2]2 with 2 equiv of (S,S)-Pfbsdpen in the presence of KOH under reflux in THF. In either case 3R or 4R was obtained as a single diastereomer, the structure of which was determined by single-crystal x-ray diffraction studies in solid state and NMR-anal. in solution Reaction mechanism was studied by NMR spectroscopy combined with continuum solvent reaction-field d. functional theory (DFT) anal. Exptl. studies showed that diastereoselective oxocyclometalation 1a → 3aR proceeds at temperatures >0° in a stepwise manner through the detectable intermediate, hydroxo complex (R)-[Ru(OH){(S,S)-Pfbsdpen}(η6-hmb)] (6aR), which exists in equilibrium with less-populated diastereomer (S)-[Ru(OH){(S,S)-Pfbsdpen}(η6-hmb)] (6aS) in 10:1 ratio at -80° in CD2Cl2. Computational anal. essentially explains the diastereoselectivity in this reaction via a significant difference in the stabilities of the corresponding transition states: although diastereomers 6aR and 6aS are in equilibrium via complex 1a, only 6aR is transformed into 3aR via rate-determining Meisenheimer-type transition state.
The article 《C-F bond breaking through aromatic nucleophilic substitution with a hydroxo ligand mediated via water bifunctional activation》 also mentions many details about this compound(313342-24-4)Recommanded Product: N-((1S,2S)-2-Amino-1,2-diphenylethyl)-2,3,4,5,6-pentafluorobenzenesulfonamide, you can pay attention to it, because details determine success or failure
Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem