A New, Expeditious Entry to the Benzophenanthrofuran Framework by a Pd-CatalyzedC- andO-Arylation/PIFA-Mediated Oxidative Coupling Sequence

2005 ◽  
Vol 2005 (12) ◽  
pp. 2481-2490 ◽  
Author(s):  
Fátima Churruca ◽  
Raul SanMartin ◽  
Imanol Tellitu ◽  
Esther Domínguez
Keyword(s):  
Oxidative Coupling ◽  
Coupling Sequence

A New, Expeditious Entry to the Benzophenanthrofuran Framework by a Pd-Catalyzed C- and O-Arylation/PIFA-Mediated Oxidative Coupling Sequence.

ChemInform ◽  
2005 ◽  
Vol 36 (42) ◽  
Author(s):  
Fatima Churruca ◽  
Raul SanMartin ◽  
Imanol Tellitu ◽  
Esther Dominguez
Keyword(s):  
Oxidative Coupling ◽  
Coupling Sequence

Base-Catalyzed Halogen Dance Reaction and Oxidative Coupling Sequence as a Convenient Method for the Preparation of Dihalo-bisheteroarenes

2010 ◽  
Vol 12 (9) ◽  
pp. 2136-2139 ◽  
Author(s):  
Yulia A. Getmanenko ◽  
Paul Tongwa ◽  
Tatiana V. Timofeeva ◽  
Seth R. Marder
Keyword(s):  
Convenient Method ◽  
Oxidative Coupling ◽  
Halogen Dance Reaction ◽  
Coupling Sequence

An Unprecedented Cyano-Induced Sodium Nitrite-Catalyzed C(sp3)-H and C(sp2)-H Coupling Reaction

2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Sodium Nitrite ◽  
Oxidative Coupling ◽  
High Resolution Mass Spectrometry ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

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.

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