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.

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.

The ‘Ireland’ one-pot alcohol oxidation coupling reactions: celebrating 30 years of diverse synthesis

2015 ◽  
Vol 13 (34) ◽  
pp. 8958-8977 ◽  
Author(s):  
Vineet Jeena ◽  
Ross S. Robinson
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Alcohol Oxidation ◽  
Coupling Reactions ◽  
One Pot ◽  
Oxidative Coupling Reaction ◽  
Oxidation Coupling

The Ireland one-pot oxidative coupling reaction is reviewed on the occasion of its 30th anniversary.

Encapsulating mesoporous metal nanoparticles: towards a highly active and stable nanoreactor for oxidative coupling reactions in water

2019 ◽  
Vol 55 (42) ◽  
pp. 5898-5901 ◽  
Author(s):  
Houbing Zou ◽  
Jinyu Dai ◽  
Runwei Wang
Keyword(s):  
Metal Nanoparticles ◽  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Efficient Production ◽  
Coupling Reactions ◽  
One Pot ◽  
Unsaturated Ketones ◽  
Oxidative Coupling Reaction ◽  
Highly Active ◽  
Mesoporous Metal

We design and prepare a highly active and stable nanoreactor by encapsulating mesoporous metal nanoparticles for efficient production of α,β-unsaturated ketones via a one-pot oxidative coupling reaction.

An Alternative Synthesis of Bipyrenol: A High-Yield Oxidative Coupling Reaction of a Pyrene Derivative with Cu(BF4)2·nH2O

Synthesis ◽  
2017 ◽  
Vol 49 (14) ◽  
pp. 3145-3148 ◽  
Author(s):  
Ken-ichi Sugiura ◽  
Subas Rajbangshi
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Previous Method ◽  
High Yield ◽  
Reaction Conditions ◽  
Marked Contrast ◽  
Alternative Synthesis ◽  
Oxidative Coupling Reaction

An alternative synthesis has been developed with the objective of extending the applications of bipyrenol in mind. The key reaction involves the oxidative coupling of 2-hydroxypyrene menthyl carbonate to afford the corresponding pyrene dimer. In marked contrast to our previous method, i.e., the oxidation of 2-hydroxypyrene, the revised method is a clean and high-yielding reaction. By optimizing the reaction conditions, the yield of the alternative synthesis is increased to 88%.

scholarly journals The substrate-dependent stereoselectivity of the multicopper oxidase (MCO)-catalyzed oxidative coupling in the biosynthesis of the bisnaphthopyrone viriditoxin

2019 ◽  
Author(s):  
Jinyu Hu ◽  
Gavin R. Flematti ◽  
Yit-Heng Chooi
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Dependent Manner ◽  
Coupling Reactions ◽  
Structural Variations ◽  
Pyrone Ring ◽  
Dirigent Protein ◽  
Oxidative Coupling Reaction ◽  
Substrate Structure ◽  
Copper Oxidase

AbstractVdtB, the multiple-copper oxidase (MCO) from the bisnaphthopyrone (M)-viriditoxin biosynthetic pathway in Paecilomyces variotii, was shown to catalyze regioselective 6,6′-coupling of semi-viriditoxin (1). The stereoselectivity of the oxidative coupling reaction for the production of the atropisomer (M)-viriditoxin, however, was controlled by VdtD, a non-catalytic dirigent protein from the pathway. In this work, VdtB either alone or together with VdtD were investigated for its stereoselective control upon coupling of other monomeric naphthopyrone derivatives from the pathway with different minor structural variations in terms of presence/absence of O-methylation at C7-position and C3-C4 Δ2 double bond on the pyrone ring, and the different side-chain modifications. We showed that VdtB could favour either M- or P-form coupling in a substrate-dependent manner. For some substrates, VdtB could catalyze oxidative coupling in an enantiomerically selective manner. The efficiency of the VdtD in exerting stereoselective control of the oxidative coupling reaction also varies between substrates. The results point to a model whereby VdtB and VdtD form a VdtB-ligand-VdtD complex in which the stereochemical outcome of the coupling reaction depends on how the substrate interacts with both proteins, based on the substrate structure. Our findings contributed to a more comprehensive understanding of dirigent protein-mediated MCO-catalyzed stereoselective oxidative coupling reactions in fungi.

NHPI- and TBAI-Co-Catalyzed Synthesis of Allylic Esters from Toluene Derivatives and Alkenes

Synlett ◽  
2018 ◽  
Vol 29 (06) ◽  
pp. 840-844 ◽  
Author(s):  
Hongmei Deng ◽  
Xueshun Jia ◽  
Jian Li ◽  
Chengliang Li ◽  
Tao Jin ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Reaction Conditions ◽  
Metal Free ◽  
Oxidative Coupling Reaction ◽  
New Strategy ◽  
Tetrabutylammonium Iodide ◽  
Allylic Esters

An N-hydroxyphthalimide (NHPI) and tetrabutylammonium iodide (TBAI) co-catalyzed oxidative coupling reaction of toluene derivatives and alkenes has been disclosed. This method can serve as a new strategy to access allylic ester using toluene derivatives as oxyacylating reagent. This metal-free protocol also features the readily available starting materials, broad substrate scope, and mild reaction conditions.

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