Regioselective Oxidative Coupling Reactions of 3-Substituted Thiophenes with Arylboronic Acids

2011 ◽  
Vol 13 (14) ◽  
pp. 3640-3643 ◽  
Author(s):  
Ingo Schnapperelle ◽  
Stefan Breitenlechner ◽  
Thorsten Bach
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reactions ◽  
Arylboronic Acids ◽  
Oxidative Coupling Reactions

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.

Catalytic oxidative coupling promoted by bismuth TEMPOxide complexes

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

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

scholarly journals Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 852 ◽  
Author(s):  
Lin-Yang Wu ◽  
Muhammad Usman ◽  
Wen-Bo Liu
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Iron Complex ◽  
Coupling Reactions ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

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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