166959-36-0Relevant academic research and scientific papers
Nickel-Catalyzed Cross-Electrophile Coupling between Benzyl Alcohols and Aryl Halides Assisted by Titanium Co-reductant
Suga, Takuya,Ukaji, Yutaka
, p. 7846 - 7850 (2019/01/14)
A nickel-catalyzed cross-electrophile coupling reaction between benzyl alcohols and aryl halides has been developed using a homolytic C-O bond cleavage protocol that has recently been established. The treatment of a benzyl alcohol and aryl halide with a nickel catalyst and low-valent titanium reagent generated from TiCl4(lutidine) (lutidine = 2,6-lutidine) and manganese powder afforded the cross-coupled product in high yield. A mechanistic study indicated the intermediacy of the benzyl radicals that originate from the benzyl alcohols.
Ring-closure reaction of 2-benzoylbenzenediazonium salts in 1-butyl-3- methylimidazolium ionic liquids
Okazaki, Takao,Yamamoto, Hiroyuki,Kitagawa, Toshikazu
, p. 50 - 59 (2018/02/07)
A ring-closure reaction by thermal dediazoniation of 2-substituted benzenediazonium tetrafluoroborates in imidazolium-based ionic liquids was investigated. Dediazoniation of 2-(4-R-benzoyl)benzenediazonium tetrafluoroborates (R = H, Me, OMe, Cl) in ionic liquid [BMIM][TfO] gave 3-R-9-fluorenones as ring-closure products and 2-(4-R-benzoyl)phenyl trifluoromethanesulfonates as substitution products. Dediazoniation in [BMIM][Tf2N] afforded 3-R-9-fluorenones and R-C6H4-CO-C6H4-OSO(CF3)(NSO2CF3). Yields of the ring-closure products were higher in [BMIM][Tf2N] than in [BMIM][TfO]. 2-Benzylbenzenediazonium and 2-phenoxybenzenediazonium tetrafluoroborates exclusively produced substitution products in both ionic liquids. DFT calculations suggest that electron transfer from the anion to render homolytic process should be induced more readily in [BMIM][Tf2N] than in [BMIM][TfO]. This ability may be responsible for the higher yields of the ring-closure products via homolytic pathway and the smaller yields of the substitution products via heterolytic pathway in [BMIM][Tf2N].
Mechanistic study of a Pd/C-catalyzed reduction of aryl sulfonates using the Mg-MeOH-NH4OAc system
Mori, Akinori,Mizusaki, Tomoteru,Ikawa, Takashi,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
, p. 1432 - 1441 (2008/02/04)
A method for the deoxygenation of phenolic hydroxy groups via aryl triflates or mesylates has been established by using a combination of Pd/ C-Mg-MeOH. The addition of NH4OAc to the system markedly accelerated the reaction rate and expanded the scope of the reaction. Mechanistic studies suggested that a single-electron transfer process from the Pd0 center to the benzene ring is involved in the reduction of aryl sulfonates and that NH4OAc works as a solubilization re agent of the Mg salt and as an accelerator of the electron transfer, thus enhancing the reaction process. Our method was also applicable to the regioselective deuteration of benzene derivatives with CH3OD as the solvent and deuterium source: the original hydroxy group could be efficiently replaced with a deuterium atom.
Synthesis of polycyclic xanthenes and furans via palladium-catalyzed cyclization of polycyclic aryltriflate esters
Wang, Ji-Quan,Harvey, Ronald G
, p. 5927 - 5931 (2007/10/03)
Palladium-catalyzed cyclization of polycyclic aromatic o-(arylmethyl)phenol triflate esters takes place with unexpected sulfur-oxygen bond cleavage to furnish polycyclic xanthenes. These are the first examples of Pd-catalyzed cross-coupling of aryl triflate esters with arenes to form diaryl ethers. In contrast, analogous palladium-catalyzed cyclization of polycyclic o-(aryloxy)phenol triflate esters proceeds via a mechanism that involves conventional carbon-oxygen bond cleavage to furnish diaryl furans.
