112-45-8Relevant articles and documents
Catalytic oxidation of alcohols into aldehydes and ketones by an osmium- copper bifunctional system using molecular oxygen
Coleman, Karl S.,Coppe, Maurice,Thomas, Christophe,Osborn, John A.
, p. 3723 - 3726 (1999)
The oxidation of allylic and benzylic alcohols to aldehydes can be carried out at room temperature as low as 25°C with molecular oxygen, in the presence of the bifunctional osmium-copper system OsO4-CuCl acting as the catalyst.
A relay ring-opening/double ring-closing metathesis strategy for the bicyclic macrolide-butenolide core structures
Halle, Mahesh B.,Fernandes, Rodney A.
, p. 63342 - 63348 (2014)
A concise strategy has been developed for the synthesis of the bicyclic macrolide-butenolide core structures of various natural products with the macrolide ring size ranging from 12- to 16-membered. The bicyclic structure was easily assembled using the relay ring-opening/double ring-closing metathesis strategy. An efficient synthesis of (±)-desmethyl manshurolide has been achieved as an application of this strategy. This journal is
Catalytic oxidation of various alcohols to the corresponding carbonyl compounds with N-chlorosuccinimide using a catalytic amount of sulfenamide
Mukaiyama, Teruaki,Matsuo, Jun-Ichi,Iida, Daisuke,Kitagawa, Hideo
, p. 846 - 847 (2001)
Various primary and secondary alcohols were smoothly oxidized to the corresponding carbonyl compounds with N-chlorosuccinimide by using a catalytic amount of N-tert-butylbenzenesulfenamide (1) in the co-existence of potassium carbonate and molecular sieves 4A.
Stereospecific synthesis of 11E-tetradecenal, 11E-tetradecen-1-ol, and its acetate, pheromone components of insects of Lepidoptera order, from 10-undecenoic acid
Ishmuratov,Yakovleva,Kharisov,Muslukhov,Tolstikov
, p. 1035 - 1037 (1997)
A regio-and stereospecific synthesis of 11E-tetradecen-1-ol and its derivatives, which are pheromone components of many insect species of Lepidoptera order, by means of a reaction of methylmagnesium cuprate reagent with 1,12-tridecadien-3-yl acetate by the SN2' mechanism, was carried out.
An isocyanide ligand for the rapid quenching and efficient removal of copper residues after Cu/TEMPO-catalyzed aerobic alcohol oxidation and atom transfer radical polymerization
Bulska, Ewa,Enciso, Alan E.,Fantin, Marco,Grela, Karol,Lorandi, Francesca,Matyjaszewski, Krzysztof,Nogas, Wojciech,Piatkowski, Jakub,Ruszczynska, Anna,Szczepaniak, Grzegorz,Yerneni, Saigopalakrishna S.
, p. 4251 - 4262 (2020)
Transition metal catalysts play a prominent role in modern organic and polymer chemistry, enabling many transformations of academic and industrial significance. However, the use of organometallic catalysts often requires the removal of their residues from reaction products, which is particularly important in the pharmaceutical industry. Therefore, the development of efficient and economical methods for the removal of metal contamination is of critical importance. Herein, we demonstrate that commercially available 1,4-bis(3-isocyanopropyl)piperazine can be used as a highly efficient quenching agent (QA) and copper scavenger in Cu/TEMPO alcohol aerobic oxidation (Stahl oxidation) and atom transfer radical polymerization (ATRP). The addition ofQAimmediately terminates Cu-mediated reactions under various conditions, forming a copper complex that can be easily separated from both small molecules and macromolecules. The purification protocol for aldehydes is based on the addition of a small amount of silica gel followed byQAand filtration. The use ofQA?SiO2synthesizedin situresults in products with Cu content usually below 5 ppm. Purification of polymers involves only the addition ofQAin THF followed by filtration, leading to polymers with very low Cu content, even after ATRP with high catalyst loading. Furthermore, the addition ofQAcompletely prevents oxidative alkyne-alkyne (Glaser) coupling. Although isocyanideQAshows moderate toxicity, it can be easily converted into a non-toxic compound by acid hydrolysis.
SBA-15 Supported 1-Methyl-2-azaadamanane N-Oxyl (1-Me-AZADO) as Recyclable Catalyst for Oxidation of Alcohol
Tian, Yangwu,Guo, Xiaqun,Li, Meichao,Li, Chunmei,Hu, Xinquan,Jin, Liqun,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu
supporting information, p. 3928 - 3932 (2021/05/26)
Herein, we designed and synthesized an SBA-15 supported 1-methyl-2-azaadamanane N-oxyl (1-Me-AZADO) and investigated its catalytic performance for selective oxidation of alcohols under Anelli's conditions. The first example of immobilization of 1-Me-AZADO was very important to advance the oxgenation effectively because this supported N-oxyl has excellent catalytic activity for oxidation of alcohols to carbonyl compounds, and more importantly, it can be conveniently recovered and reused at least 6 times without significant effect on its catalytic efficiency.
3-BocNH-ABNO-catalyzed aerobic oxidation of alcohol at room temperature and atmospheric pressure
Zhao, Yajing,Li, Yutong,Shen, Zhenlu,Hu, Xinquan,Hu, Baoxiang,Jin,Sun, Nan,Li, Meichao
supporting information, (2019/08/06)
A transition-metal-free catalytic system has been developed for selective transformation of alcohol to aldehydes or ketones. The reactions were performed with 3-(tert-butoxycarbonylamino)-9-azabicyclo[3.3.1]nonane N-oxyl (3-BocNH-ABNO) as the catalyst, NaNO2 as the co-catalyst, molecular oxygen as the terminal oxidant, and AcOH as the solvent under room temperature. This catalytic system exhibited broad functional group tolerance. A series of alcohol substrates, including primary and secondary benzylic alcohols, heteroaromatic analogues, primary and secondary aliphatic alcohols, could be converted into their corresponding aldehydes and ketones in good conversions and selectivities.
