726-18-1Relevant articles and documents
Deoxygenation of tertiary and secondary alcohols with sodium borohydride, trimethylsilyl chloride, and potassium iodide in acetonitrile
Kato, Yuichi,Inoue, Tomoka,Furuyama, Yuuki,Ohgane, Kenji,Sadaie, Mahito,Kuramochi, Kouji
supporting information, (2021/11/16)
The deoxygenation of tertiary and secondary alcohols to give the corresponding alkanes is conventionally performed using an organosilane and a strong acid. In this study, a deoxygenation method was developed for tertiary and secondary alcohols, using trimethylsilane and trimethylsilyl iodide generated in situ from sodium borohydride and trimethylsilyl chloride, and trimethylsilyl chloride and potassium iodide, respectively. With our method, tertiary and secondary alcohols, which provided stable carbocations, were converted into the corresponding alkanes. This paper also presents the optimization of the reaction conditions, the reaction mechanism, as well as the scope and limitations of the method.
Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis
Guo, Peng,Wang, Ke,Jin, Wen-Jie,Xie, Hao,Qi, Liangliang,Liu, Xue-Yuan,Shu, Xing-Zhong
, p. 513 - 523 (2021/01/12)
Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.
Preparation of a platinum nanoparticle catalyst located near photocatalyst titanium oxide and its catalytic activity to convert benzyl alcohols to the corresponding ethers
Akiyama, Toshiki,Arisawa, Mitsuiro,Harada, Kazuo,Honma, Tetsuo,Naka, Hiroshi,Saito, Susumu,Wada, Yuki
, p. 22230 - 22237 (2021/07/02)
A novel platinum nanoparticle catalyst closely located near the surface of titanium oxide, PtNP/TiO2, has been prepared. This catalyst has both the properties of a photocatalyst and a metal nanoparticle catalyst, and acquired environmentally friendly catalytic activity, which cannot be achieved by just one of these catalysts, to afford ethers from benzyl alcohols under the wavelength of 420 nm.
