Comparison of the Oxidative Coupling Reactions of Benzene with Those of Methane of Rare Earth Oxide Catalysts

1994 ◽  
Vol 67 (12) ◽  
pp. 3339-3345 ◽  
Author(s):  
Shigeru Sugiyama ◽  
Takashi Ookubo ◽  
Kazuaki Shimodan ◽  
Hiromu Hayashi ◽  
John B. Moffat
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.


Fuel ◽  
1998 ◽  
Vol 77 (13) ◽  
pp. 1477-1481 ◽  
Author(s):  
Vasant R. Choudhary ◽  
Bathula Prabhakar ◽  
Amarjeet M. Rajput ◽  
Ajit S. Mamman

2009 ◽  
Vol 352 (1-2) ◽  
pp. 66-73 ◽  
Author(s):  
Hirotomo Inoue ◽  
Satoshi Sato ◽  
Ryoji Takahashi ◽  
Yusuke Izawa ◽  
Hironobu Ohno ◽  
...  

2018 ◽  
Vol 54 (8) ◽  
pp. 916-919 ◽  
Author(s):  
R. J. Schwamm ◽  
M. Lein ◽  
M. P. Coles ◽  
C. M. Fitchett

Bismuth(iii) TEMPOxide complexes are active catalysts for oxidative coupling reactions to generate TEMPO silylethers.


Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 852 ◽  
Author(s):  
Lin-Yang Wu ◽  
Muhammad Usman ◽  
Wen-Bo Liu

An iron-catalyzed asymmetric oxidative homo-coupling of 2-naphthols for the synthesis of 1,1′-Bi-2-naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron-complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)-N1,N2-di(quinolin-8-yl)cyclohexane-1,2-diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.


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