TEMPO-Enabled Electrochemical Enantioselective Oxidative Coupling of Secondary Acyclic Amines with Ketones

Author(s):  
Zhen-Hua Wang ◽  
Pei-Sen Gao ◽  
Xiu Wang ◽  
Jun-Qing Gao ◽  
Xue-Tao Xu ◽  
...  
Keyword(s):  
2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.


2019 ◽  
Vol 9 (6) ◽  
pp. 1349-1356 ◽  
Author(s):  
Johnny Zhu Chen ◽  
Zhenwei Wu ◽  
Xiaoben Zhang ◽  
Slgi Choi ◽  
Yang Xiao ◽  
...  

Identification of a Pt3Bi nanoscale, surface intermetallic alloy catalyst for non-oxidative coupling of methane (NOCM).


2015 ◽  
Vol 44 (4) ◽  
pp. 1612-1626 ◽  
Author(s):  
Pedro Adão ◽  
Sónia Barroso ◽  
M. Fernanda N. N. Carvalho ◽  
Carlos M. Teixeira ◽  
Maxim L. Kuznetsov ◽  
...  

Several chiral amino acid-derived CuII complexes were prepared and used as catalysts in the aerobic oxidative coupling of 2-naphthol. Moderate homocoupling product yields and enantiomeric excesses were obtained under mild, aqueous conditions.


2021 ◽  
Author(s):  
P. Saychu ◽  
M. Thanasiriruk ◽  
C. Khajonvittayakul ◽  
R. Viratikul ◽  
V. Tongnan ◽  
...  

Catalysts ◽  
2021 ◽  
Vol 11 (3) ◽  
pp. 388
Author(s):  
Yuqiao Fan ◽  
Changxi Miao ◽  
Yinghong Yue ◽  
Weiming Hua ◽  
Zi Gao

In this work, Ho2O3 nanosheets were synthesized by a hydrothermal method. A series of Sr-modified Ho2O3 nanosheets (Sr-Ho2O3-NS) with a Sr/Ho molar ratio between 0.02 and 0.06 were prepared via an impregnation method. These catalysts were characterized by several techniques such as XRD, N2 adsorption, SEM, TEM, XPS, O2-TPD (temperature-programmed desorption), and CO2-TPD, and they were studied with respect to their performances in the oxidative coupling of methane (OCM). In contrast to Ho2O3 nanoparticles, Ho2O3 nanosheets display greater CH4 conversion and C2-C3 selectivity, which could be related to the preferentially exposed (222) facet on the surface of the latter catalyst. The incorporation of small amounts of Sr into Ho2O3 nanosheets leads to a higher ratio of (O− + O2−)/O2− as well as an enhanced amount of chemisorbed oxygen species and moderate basic sites, which in turn improves the OCM performance. The optimal catalytic behavior is achievable on the 0.04Sr-Ho2O3-NS catalyst with a Sr/Ho molar ratio of 0.04, which gives a 24.0% conversion of CH4 with 56.7% selectivity to C2-C3 at 650 °C. The C2-C3 yield is well correlated with the amount of moderate basic sites present on the catalysts.


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