87310-12-1Relevant academic research and scientific papers
Aerobic oxidation and oxidative esterification of alcohols through cooperative catalysis under metal-free conditions
Karimi, Babak,Ghahremani, Mina,Vali, Hojatollah,Ciriminna, Rosaria,Pagliaro, Mario
supporting information, p. 8897 - 8900 (2021/09/10)
The ABNO@PMO-IL-Br material obtained by anchoring 9-azabicyclo[3.3.1]nonane-3-oneN-oxyl (keto-ABNO) within the mesopores of periodic mesoporous organosilica with bridged imidazolium groups is a robust bifunctional catalyst for the metal-free aerobic oxidation of numerous primary and secondary alcohols under oxygen balloon reaction conditions. The catalyst, furthermore, can be successfully employed in the first metal-free self-esterification of primary aliphatic alcohols affording valued esters.
Dehydrogenative alcohol coupling and one-pot cross metathesis/dehydrogenative coupling reactions of alcohols using Hoveyda-Grubbs catalysts
?zer, Halenur,Arslan, Dilan,?ztürk, Bengi ?zgün
, p. 5992 - 6000 (2021/04/12)
In this study,in situformed ruthenium hydride species that were generated from Grubbs type catalysts are used as efficient catalysts for dehydrogenative alcohol coupling and sequential cross-metathesis/dehydrogenative coupling reactions. The selectivity of Grubbs first generation catalysts (G1) in dehydrogenative alcohol coupling reactions can be tuned for the ester formation in the presence of weak bases, while the selectivity can be switched to the β-alkylated alcohol formation using strong bases. The performance of Hoveyda-Grubbs 2nd generation catalyst (HG2) was improved in the presence of tricyclohexylphosphine for the selective synthesis of ester derivatives with weak and strong bases in quantitative yields. Allyl alcohol was used as self and cross-metathesis substrate for the HG2 catalyzed sequential cross-metathesis/dehydrogenative alcohol coupling reactions to obtain γ-butyrolactone and long-chain ester derivatives in quantitative yields.
Aerobic Self-Esterification of Alcohols Assisted by Mesoporous Manganese and Cobalt Oxide
Moharreri, Ehsan,Biswas, Sourav,Deljoo, Bahareh,Kriz, David,Lim, Seyoung,Elliott, Sarah,Dissanayake, Shanka,Dabaghian, Marina,Aindow, Mark,Suib, Steven L.
, p. 3413 - 3422 (2019/08/01)
Aerobic self-esterification of primary alcohols catalyzed by mesoporous metal oxides (manganese and cobalt oxides) is reported under base and solvent free conditions. For a range of aliphatic alcohols, up to 90 % conversions to esters was achieved. The catalytic reaction is likewise applicable to neat aldehydes as substrates with yields of up to 86 %. High pressure batch reaction for ethanol to ethyl acetate led to 22 % yield. Isotope labeling studies indicated decarboxylation on the catalyst surface. Mechanistic and kinetic experiments implicate oxygen rebound and α-carbon removal as intermediate steps. Mesoporous cobalt oxide showed about 20 % higher catalytic activity compared to mesoporous manganese oxide.
Oxidative esterification of primary alcohols at room temperature under aqueous medium
Reddy, N. Naresh Kumar,Ravi, Chitrakar,Adimurthy, Subbarayappa
, p. 1663 - 1670 (2018/06/15)
Oxidative esterification of aliphatic primary alcohols with bromide and bromate couple in aqueous acidic medium at room temperature is reported with a wide range of substrate scope for both aliphatic and cyclic alcohols and obtained excellent yields of products.
Cobalt-Catalyzed Acceptorless Dehydrogenative Coupling of Primary Alcohols to Esters
Paudel, Keshav,Pandey, Bedraj,Xu, Shi,Taylor, Daniela K.,Tyer, David L.,Torres, Claudia Lopez,Gallagher, Sky,Kong, Lin,Ding, Keying
supporting information, p. 4478 - 4481 (2018/08/09)
A novel catalytic system with a tripodal cobalt complex is developed for efficiently converting primary alcohols to esters. KOtBu is found essential to the transformation. A preliminary mechanistic study suggests a plausible reaction route that involves an initial Co-catalyzed dehydrogenation of alcohol to aldehyde, followed by a Tishchenko-type pathway to ester mediated by KOtBu.
A TEMPO-like nitroxide combined with an alkyl-substituted pyridine: An efficient catalytic system for the selective oxidation of alcohols with iodine
Kashparova, Vera P.,Klushin, Victor A.,Zhukova, Irina Yu.,Kashparov, Igor S.,Chernysheva, Daria V.,Il'chibaeva, Irina B.,Smirnova, Nina V.,Kagan, Efim Sh.,Chernyshev, Victor M.
supporting information, p. 3517 - 3521 (2017/10/05)
An efficient method for the oxidation of alcohols to aldehydes or ketones in a two-phase CH2Cl2/NaHCO3 (aq.) system, using iodine and catalytic amounts of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl and 2,4,6-trimethylpyridine, was developed. The performance of the method was demonstrated by the selective oxidation of 37 variously substituted alcohols in ≥90% yield, including the gram-scale synthesis of the important chemical 2,5-diformylfuran from biomass-derived 5-hydroxylmethylfurfural.
One-pot electrochemical synthesis of acid anhydrides from alcohols
Kashparova,Papina,Kashparov,Zhukova, I. Yu.,Ilchibaeva,Kagan, E. Sh.
, p. 2733 - 2735 (2017/12/26)
One-pot indirect electrochemical oxidation of alcohols in the methylene chloride–aqueous solution of sodium hydrocarbonate two-phase system in the presence of potassium iodide, 4-acetylamino-2,2,6,6-tetramethylpiperidin-1-oxyl, and 2,6-lutidine results in
Oxidative dimerization of alcohols in the presence of nitroxyl radical–iodine catalytic system
Kashparova,Kashparov,Zhukova, I. Yu.,Astakhov,Ilchibaeva,Kagan, E. Sh.
, p. 2423 - 2426 (2016/12/24)
Pyridine catalyzes oxidation of alcohols with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl–iodine catalytic system at room temperature. Symmetric esters are formed in good yields.
Non-plasmonic metal nanoparticles as visible light photocatalysts for the selective oxidation of aliphatic alcohols with molecular oxygen at near ambient conditions
Tana, Tana,Guo, Xiao-Wei,Xiao, Qi,Huang, Yiming,Sarina, Sarina,Christopher, Phillip,Jia, Jianfeng,Wu, Haishun,Zhu, Huaiyong
, p. 11567 - 11570 (2016/10/03)
Nanoparticles (NPs) of Pd and Pt were used for the selective oxidation of aliphatic alcohols with molecular oxygen as an oxidant at near ambient temperatures under visible light irradiation. Distinct final products were obtained under identical reaction conditions, aliphatic esters formed over the Pd NPs while aldehydes formed over the Pt NPs. The reason for this different product selectivity is proven to be due to the much stronger interaction of Pd NPs with alcohol and aldehyde compared to Pt NPs. The photocatalytic activity is tuneable by light intensity or a moderate change in the reaction temperature.
Highly efficient self-esterification of aliphatic alcohols using supported gold nanoparticles under mild conditions
Wang, Fan,Xiao, Qi,Han, Pengfei,Sarina, Sarina,Zhu, Huaiyong
, p. 61 - 69 (2016/07/06)
Long aliphatic esters were prepared by the one-step catalytic self-esterification of primary alcohols using molecular oxygen as a green oxidant and supported gold nanoparticles (Au NPs) as catalyst. This heterogeneous catalyst achieved high activity and selectivity in a wide range of less reactive straight-chain alcohols (C4-C12) at atmospheric pressure O2 and near ambient temperature (45?°C). Under optimised conditions, the catalyst with Au loading of 3?wt% achieved the highest catalytic activity and selectivity. The AuNP catalysts are efficient and readily recyclable. The finding of this study may inspire further studies on new efficient catalytic systems for a wide range of organic syntheses using supported AuNP catalysts.
