Hikawa, Hidemasa’s team published research in Advanced Synthesis & Catalysis in 2015 | CAS: 6214-45-5

Advanced Synthesis & Catalysis published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, Computed Properties of 6214-45-5.

Hikawa, Hidemasa published the artcilePalladium-Catalyzed Benzylic C-H Benzylation via Bis-Benzylpalladium(II) Complexes in Water: An Effective Pathway for the Direct Construction of N-(1,2-Diphenylethyl)anilines, Computed Properties of 6214-45-5, the main research area is aniline diphenylethyl preparation; benzyl alc aniline benzylation palladium catalyst.

A strategy for the N-benzylation/benzylic C-H benzylation cascade of anilines by the π-benzylpalladium system using a water-soluble palladium(0)/sodium diphenylphosphinobenzene-3-sulfonate (TPPMS) catalyst and benzyl alc. in water has been developed. The nucleophilic ν1-σ-benzyl anion ligand attacks the electrophilic ν3-π-benzyl ligand to give a dibenzylated product. The intermol. competition between mono-N-benzylaniline and its monodeuterated form (monodeuterated at the benzylic group) with benzyl alc. gave a KIE = 4.6, suggesting that C-H bond cleavage was involved in the rate-determining step. Hammett studies on the rate constants of benzylation by various substituted anthranilic acids and mono-N-benzylanilines show a good correlation between the log(kX/kH) and the σ values of the resp. substituents. From the slope, neg. ρ values were obtained, suggesting that there is a build-up of pos. charge in the transition state. The reaction of anilines R1C6H4NH2 (R1 = 4-Me, 3-COOEt, 2-OPh, etc.) with electron-donating and electron-withdrawing groups R2C6H4CH2 (R2 = H, 4-MeO, 3-Me, etc.) afforded the corresponding N-(1,2-diphenylethyl)anilines I in moderate to good yields (54-86%). Interestingly, the reaction of anthranilic acids R3C6H3(COOH)NH2 (R3 = 6-Me, 5-NHAc, H, etc.) with benzylic alcs. R4CH2OH (R4 = Ph, naphthyl, 4-MeC6H4, 3-MeC6H4) proceeded smoothly to give only the corresponding dibenzylated products II in good to excellent yields (70-87%) in which carboxyl group of the anthranilic acids acts as a directing group.

Advanced Synthesis & Catalysis published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, Computed Properties of 6214-45-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts