17714-41-9Relevant academic research and scientific papers
Direct Reduction of Allylic Alcohols Using Isopropanol as Reductant
Sai, Masahiro
, p. 3482 - 3487 (2018/09/14)
The lithium cation-catalyzed direct reduction of allylic alcohols to alkenes using isopropanol as a hydride donor was developed. The hydride transfer of the in situ-generated lithium isopropoxide to an allylic cation is the key process in this transformation. The reaction generates only water and acetone as byproducts, which highlights the synthetic utility of this method. (Figure presented.).
Fluorinated alcohols as promoters for the metal-free direct substitution reaction of allylic alcohols with nitrogenated, silylated, and carbon nucleophiles
Trillo, Paz,Baeza, Alejandro,Najera, Carmen
, p. 7344 - 7354 (2012/10/30)
The direct allylic substitution reaction using allylic alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE) as reaction media is described. The developed procedure is simple, works under mild conditions (rt, 50 and 70 °C), and proves to be very general, since different nitrogenated nucleophiles and carbon nucleophiles can be used achieving high yields, especially when HFIP is employed as solvent and aromatic allylic alcohols are the substrates. Thus, sulfonamides, carbamates, carboxamides, and amines can be successfully employed as nitrogen-based nucleophiles. Likewise, silylated nucleophiles such as trimethylsilylazide, allyltrimethylsilane, trimethylsilane, and trimethylsilylphenylacetylene give the corresponding allylic substitution products in high yields. Good results for the Friedel-Crafts adducts are also achieved with aromatic compounds (phenol, anisole, indole, and anilines) as nucleophiles. Particularly interesting are the results obtained with electron-rich anilines, which can behave as nitrogenated or carbon nucleophiles depending on their electronic properties and the solvent employed. In addition, 1,3-dicarbonyl compounds (acetylacetone and Meldrum's acid) are also successfully employed as soft carbon nucleophiles. Studies for mechanism elucidation are also reported, pointing toward the existence of carbocationic intermediates and two working reaction pathways for the obtention of the allylic substitution product.
FeCl3 · 6H2O catalyzed disproportionation of allylic alcohols and selective allylic reduction of allylic alcohols and their derivatives with benzyl alcohol
Wang, Jialiang,Huang, Wen,Zhang, Zhengxing,Xiang, Xu,Liu, Ruiting,Zhou, Xigeng
body text, p. 3299 - 3304 (2009/09/08)
Iron chloride has been found to be an efficient catalyst for the disproportionation of allylic alcohols, which provides a convenient method for selective transformation of allylic alcohols to alkenes and α,β- unsaturated ketones. Furthermore, this catalytic system is also effective for highly selective allylic reduction of allylic alcohols, allylic ethers, and allylic acetates with benzyl alcohol under neutral and convenient reaction conditions.
An efficient molybdenum(VI)-catalyzed direct substitution of allylic alcohols with nitrogen, oxygen, and carbon nucleophiles
Yang, Hongwei,Fang, Ling,Zhang, Ming,Zhu, Chengjian
experimental part, p. 666 - 672 (2009/07/17)
Direct nucleophilic substitution of allylic alcohols with various nitrogen, oxygen, and carbon nucleophiles catalyzed by MoO2(acac)2 was realized. The corresponding products were obtained in moderate-to-excellent yields. Studies of t
Stereo- and chemoselective transfer hydrogenation of carbonyl groups with RuCl2(PPh3)3 and BINAP-Ru as catalysts and et3NH+H2PO2-·1,5H 2O as a hydrogen donor
Khai, Bui The,Arcelli, Antonio
, p. 6599 - 6602 (2007/10/03)
Using Et3NH+H2PO2-.1.5 H2O as a hydrogen donor, the RuCl2(Ph3P)3, RuCl2(PPh3)3 / C and BINAP-Ru proved highly active catalysts for transfer hydrogenation of ketones under milder conditions than other hydrogen donors. 2-Methyl-, 2-chloro-, 2-(ethoxycarbonyl)cyclohexanones and -cyclopentanones were reduced to the less stable axial alcohols in excellent diastereoisomeric excess (de: 90-100%), and the carbonyl group of α,β-unsaturated ketones was selectively reduced, in contrast with other hydrogen donors the C=C bond was reduced. Copyright
