Highly practical sodium(i)/azobenzene catalyst system for aerobic oxidation of benzylic alcohols

RSC Advances ◽  
2015 ◽  
Vol 5 (97) ◽  
pp. 79699-79702 ◽  
Author(s):  
Chengkou Liu ◽  
Zheng Fang ◽  
Zhao Yang ◽  
Qingwen Li ◽  
Shiyu Guo ◽  
...  

An aerobic alcohol oxidation system was described firstly. The corresponding carbonyl compounds and acids were obtained respectively in good yields.

2016 ◽  
Vol 14 (2) ◽  
pp. 577-581 ◽  
Author(s):  
Chengkou Liu ◽  
Zheng Fang ◽  
Zhao Yang ◽  
Qingwen Li ◽  
Shiyu Guo ◽  
...  

A new aerobic alcohol oxidation system of AIBN/NaBr was described for the first time. Moreover, a radical mechanism was assumed and confirmed.


2010 ◽  
Vol 49 (2) ◽  
pp. 436-440 ◽  
Author(s):  
Yongbo Kuang ◽  
Nazrul M. Islam ◽  
Yuta Nabae ◽  
Teruaki Hayakawa ◽  
Masa‐aki Kakimoto

2019 ◽  
Vol 21 (6) ◽  
pp. 1401-1405 ◽  
Author(s):  
Xiu-Jie Yang ◽  
Yi-Wen Zheng ◽  
Li-Qiang Zheng ◽  
Li-Zhu Wu ◽  
Chen-Ho Tung ◽  
...  

A simple and environmentally benign visible-light-driven dehydrogenation of benzylic alcohols with H2 as the only byproduct is achieved by using an eosin Y and nickel–thiolate complex dual catalyst system.


2012 ◽  
Vol 42 (15) ◽  
pp. 2318-2326 ◽  
Author(s):  
Kaihui Yu ◽  
Dongnai Ye ◽  
Lei Shu ◽  
Shiyong Zhang ◽  
Qiaosheng Hu ◽  
...  

2009 ◽  
Vol 122 (2) ◽  
pp. 446-450 ◽  
Author(s):  
Yongbo Kuang ◽  
Nazrul M. Islam ◽  
Yuta Nabae ◽  
Teruaki Hayakawa ◽  
Masa‐aki Kakimoto

Inorganics ◽  
2018 ◽  
Vol 6 (3) ◽  
pp. 75 ◽  
Author(s):  
Justin Mobley ◽  
John Jennings ◽  
Tonya Morgan ◽  
Axel Kiefer ◽  
Mark Crocker

Alcohol oxidation to carbonyl compounds is one of the most commonly used reactions in synthetic chemistry. Herein, we report the use of base metal layered double hydroxide (LDH) catalysts for the oxidation of benzylic alcohols in polar solvents. These catalysts are ideal reagents for alcohol oxidations due to their ease of synthesis, tunability, and ease of separation from the reaction medium. LDHs synthesized in this study were fully characterized by means of X-ray diffraction, NH3-temperature programmed desorption (TPD), pulsed CO2 chemisorption, N2 physisorption, electron microscopy, and elemental analysis. LDHs were found to effectively oxidize benzylic alcohols to their corresponding carbonyl compounds in diphenyl ether, using O2 as the terminal oxidant. LDH catalysts were also applied to the oxidation of lignin β-O-4 model compounds. Typically, for all catalysts, only trace amounts of the ketone formed from benzylic alcohol oxidation were observed, the main products comprising benzoic acids and phenols arising from β-aryl ether cleavage. This observation is consistent with the higher reactivity of the ketones, resulting from weakening of the Cβ–O4 bond that was shown to be aerobically cleaved at 180 °C in the absence of a catalyst.


Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 315-318
Author(s):  
Yuta Matsukawa ◽  
Tsunehisa Hirashita

A new aerobic oxidation system consisting of Cu(I)I, 2,2'-bipyridine, N-methyl imidazole, and a mesoionic hydroxyamide was developed, with which selective oxidation of a broad range of benzylic alcohols was achieved.


2018 ◽  
Vol 14 ◽  
pp. 971-978 ◽  
Author(s):  
Takayuki Yakura ◽  
Tomoya Fujiwara ◽  
Akihiro Yamada ◽  
Hisanori Nambu

Several N-isopropyliodobenzamides were evaluated as catalysts for the oxidation of benzhydrol to benzophenone in the presence of Oxone® (2KHSO5·KHSO4·K2SO4) as a co-oxidant at room temperature. A study on the substituent effect of the benzene ring of N-isopropyl-2-iodobenzamide on the oxidation revealed that its reactivity increased in the following order of substitution: 5-NO2 < 5-CO2Me, 3-OMe < 5-OAc < 5-Cl < H, 4-OMe < 5-Me < 5-OMe. The oxidation of various benzylic and aliphatic alcohols using a catalytic amount of the most reactive 5-methoxy derivative successfully resulted in moderate to excellent yields of the corresponding carbonyl compounds. The high reactivity of the 5-methoxy derivative at room temperature is a result of the rapid generation of the pentavalent species from the trivalent species during the reaction. 5-Methoxy-2-iodobenzamide would be an efficient and environmentally benign catalyst for the oxidation of alcohols, especially benzylic alcohols.


ChemInform ◽  
2010 ◽  
Vol 41 (18) ◽  
Author(s):  
Yongbo Kuang ◽  
Nazrul M. Islam ◽  
Yuta Nabae ◽  
Teruaki Hayakawa ◽  
Masa-aki Kakimoto

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