74562-99-5Relevant academic research and scientific papers
An expedient, efficient and solvent-free synthesis of T3P-mediated amidation of benzhydrols with poorly reactive N-nucleophiles under MW irradiation
Cheruku, Srinivas,Manikyanally, Kumara N.,Mantelingu, Kempegowda,Nagarakere, Sandhya C.,Narayana, Yatheesh,Rangappa, Kanchugarakoppal S.,Sunilkumar, Makanahalli P.
, p. 4421 - 4426 (2022/03/14)
An expedient, efficient, economical, environmentally benign, and solvent free amidation protocol of benzhydrols with less reactive nitrogen nucleophiles assisted by propylphosphonic anhydride (T3P) under microwave irradiation has been developed. The methodology has been deployed for a wide range of heterocycles and electron-withdrawing & electron-donating groups. The protocol resulted in good to excellent yields under the given conditions (26 examples, 68-93% yield).
Deoxygenation of tertiary and secondary benzylic alcohols into alkanes with triethylsilane catalyzed by solid acid tin(IV) ion-exchanged montmorillonite
Tandiary, Michael Andreas,Masui, Yoichi,Onaka, Makoto
supporting information, p. 4160 - 4162 (2014/07/22)
We discovered an efficient protocol for the conversion of tertiary and secondary benzylic alcohols into the corresponding alkanes in good to quantitative yields by employing tin(IV) ion-exchanged montmorillonite (Sn-Mont) as a solid acid catalyst and Et3SiH as the hydride source. The reaction is likely to proceed via the SN1-type reaction mechanism, that is, the formation of carbenium ions, followed by the addition of a hydride from the silane. The work-up of the reaction only requires simple filtration of the solid acid without any neutralization of the acid catalyst.
Organic reactions catalyzed by methylrhenium trioxide: Dehydration, amination, and disproportionation of alcohols
Zhu, Zuolin,Espenson, James H.
, p. 324 - 328 (2007/10/03)
Methylrhenium trioxide (MTO) is the first transition metal complex in trace quantity to catalyze the direct formation of ethers from alcohols. The reactions are independent of the solvents used: benzene, toluene, dichloromethane, chloroform, acetone, and in the alcohols themselves. Aromatic alcohols gave better yields than aliphatic. Reactions between two different alcohols could also be used to prepare unsymmetric ethers, the best yields being obtained when one of the alcohols is aromatic. MTO also catalyzes the dehydration of alcohols to form olefins at room temperature, aromatic alcohols proceeding in better yield. When primary (secondary) amines were used as the limiting reagent, direct amination of alcohols catalyzed by MTO gave good yields of the expected secondary (tertiary) amines at room temperature. Disproportionation of alcohols to alkanes and carbonyl compounds was also observed for aromatic alcohols in the presence of MTO. On the basis of the results of this investigation and a comparison with the interaction between MTO and water, a concerted process and a mechanism involving carbocation intermediates have been suggested.
CARBOXYLATION OF ALCOHOLS WITH CARBON MONOXIDE SUPERSATURATED IN STRONG ACID. FACILE SYNTHESIS OF 2,2-BIS(4-HALOPHENYL)ACETIC, -PROPIONIC, AND RELATED ACIDS
Takahashi, Yukio,Yoneda, Norihiko,Nagai, Hiroshi
, p. 1733 - 1734 (2007/10/02)
Using 97percent H2SO4 supersaturated with carbon monoxide, bis(4-halophenyl)methanols, 1,1-bis(4-halophenyl)ethanols and related alcohols were transformed to the carboxylic acids in 60-95percent yields.
Transformation of Carbinols by RuCl2(PPh3)3 and by Some Other Transition-Metal Catalysts
Pri-Bar, Ilan,Buchman, Ouri,Schumann, Hebert,Kroth, Heinz J.,Blum, Jochanan
, p. 4418 - 4428 (2007/10/02)
Several platinoid metal catalysts have been shown to promote reductive coupling, dehydration, disproportionation, and dehydrogenation of diarylcarbinols.Mechanistic studies were performed at 180-210 deg C with benzhydrol as substrate and RuCl2(PPh3)3 as catalyst.In aromatic hydrocarbon solvents the main process is reductive coupling.In this medium solvated RuCl2(PPh3)2 is suggested to be the active catalyst.In dimethyl sulfoxide the starting complex is transformed initially into RuCl2(PPh3)(Me2SO)2 and causes chiefly carbinol dehydrogenation.Ruthenium alkoxides are implied as common reaction intermediates in all four catalyses.Ruthenium hydrides are suggested to take part in the reductive coupling, disproportionation, and dehydrogenation processes.Some aliphatic and primary aromatic alcohols that do not react by themselves in the presence of RuCl2(PPh3)3 can both serve as active hydrogen donors and form crossover products in the presence of secondary and tertiary aromatic carbinols.
