1237-68-9Relevant articles and documents
Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes
Iosub, Andrei V.,Morav?ík, ?tefan,Wallentin, Carl-Johan,Bergman, Joakim
, p. 7804 - 7808 (2019/10/14)
The direct reduction of carboxylic acids to aldehydes is a fundamental transformation in organic synthesis. The combination of an air-stable Ni precatalyst, dimethyl dicarbonate as an activator, and silane reductant effects this reduction for a wide variety of substrates, including pharmaceutically relevant structures, in good yields and with no overreduction to alcohols. Moreover, this methodology is scalable, allows access to deuterated aldehydes, and is also compatible with one-pot utilization of the aldehyde products.
Selective Hydrosilylation of Esters to Aldehydes Catalysed by Iridium(III) Metallacycles through Trapping of Transient Silyl Cations
Corre, Yann,Rysak, Vincent,Capet, Frédéric,Djukic, Jean-Pierre,Agbossou-Niedercorn, Francine,Michon, Christophe
, p. 14036 - 14041 (2016/09/21)
The combination of an iridium(III) metallacycle and 1,3,5-trimethoxybenzene catalyses rapidly and selectively the reduction of esters to aldehydes at room temperature with high yields through hydrosilylation followed by hydrolysis. The ester reduction involves the trapping of transient silyl cations by the 1,3,5-trimethoxybenzene co-catalyst, supposedly by formation of an arenium intermediate whose role was addressed by DFT calculations.
Preparation, X-ray structure, and reactivity of 2-iodylpyridines: Recyclable hypervalent iodine(V) reagents
Yoshimura, Akira,Banek, Christopher T.,Yusubov, Mekhman S.,Nemykin, Victor N.,Zhdankin, Viktor V.
, p. 3812 - 3819 (2011/07/08)
2-Iodylpyridine and four examples of 3-alkoxy-2-iodylpyridines were prepared by oxidation of the respective 2-iodopyridines with 3,3-dimethyldioxirane. Structures of 2-iodylpyridine, 2-iodyl-3- isopropoxypyridine, and 2-iodyl-3-propoxypyridine were established by single-crystal X-ray diffraction analysis. 2-Iodyl-3-propoxypyridine has moderate solubility in organic solvents (e.g., 1.1 mg/mL in acetonitrile) and can be used as a recyclable reagent for oxidation of sulfides and alcohols. The reduced form of this reagent, 2-iodo-3-propoxypyridine, can be effectively separated from the reaction mixture by treatment with diluted sulfuric acid and recovered from the acidic aqueous solution by adding aqueous sodium hydroxide.