60544-10-7

Upstream product

• 766-47-2 1-ethynyl-2-methylbenzene 
• 615-37-2 ortho-methylphenyl iodide 
• 130-15-4 [1,4]naphthoquinone 
• 16419-60-6 2-Methylphenylboronic acid 
• 108-88-3 toluene 
• 1374643-16-9 bis(2-methylphenyl)iodonium trifluoromethanesulfonic acid 

Relevant academic research and scientific papers

Synthesis of aryl- and alkylquinones through rhodium-catalyzed C-C coupling under mild conditions

A direct arylation, alkylation of quinones with aryl and alkyl boronic acids through rhodium-catalyzed C-C coupling has been developed under mild conditions. [CpRhCl2]2 was shown to be the most effective catalyst for the transformation. More importantly, good to excellent yields were obtained under room temperature and base-free conditions. This reaction provides a practical, efficient method for the synthesis of aryl- and alkylquinones.

Palladium-catalyzed arylation of 1,4-naphthoquinones with aryl iodides and its synthetic application to the benzo[b]phenanthridine skeleton

We report a Pd-catalyzed arylation of 1,4-naphthoquinones with aryl iodides. This reaction shows excellent functional group tolerance and high regioselectivity when using nonsymmetric 1,4-naphthoquinone. Furthermore, the resulting 2-aryl-1,4-naphthoquinon

CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones

A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance.

Synthetic method for 2-substituted-1,4-naphthoquinone derivatives

The invention discloses a synthetic method for 2-substituted-1,4-naphthoquinone derivatives. The method comprises the following steps: with 2-alkynylacetophenone compounds as shown in a formula I which is described in the specification as a raw material and dimethyl sulfoxide as an oxidizing agent and a solvent, carrying out a reaction at 80 to 140 DEG C under stirring and the action of a copper catalyst for 2 to 10 h; and subjecting a reaction solution obtained after completion of the reaction to post-treatment so as to obtain the 2-substituted-1,4-naphthoquinone derivatives as shown in a formula II which is described in the specification, wherein the copper catalyst is a mixture of bis(copper trifluoromethanesulfonate) and an inorganic cuprous salt, and the inorganic cuprous salt is one selected from a group consisting of cuprous iodide, cuprous chloride, cuprous bromide and cuprous cyanide. The method has the advantages that the raw materials are variable; the number of the prepared derivatives is great; the catalyst is cheap and easily available; cost is substantially reduced; no pollution is produced; no extra oxidizing agent is needed; dimethyl sulfoxide both functions as the oxygen source and the solvent, so cost is saved; and the method has the characteristics of high reaction yield, good substrate applicability, simple operation, etc.

Method for synthesizing 2-substituted-1,4-naphthoquinone compound

The invention discloses a method for synthesizing a 2-substituted-1,4-naphthoquinone compound. The method comprises the following steps: by taking a 2-alkynyl acetophenone compound of a formula I as shown in the specification as a raw material, in the presence of a copper catalyst, by taking Selectfluor as an oxidant, adding an alkali substance, performing a stirring reaction for 10-24 hours at 70 DEG C in a mixed solvent of acetonitrile and water, and after the reaction is completed, and performing aftertreatment on reaction liquid, thereby obtaining the 2-substituted-1,4-naphthoquinone compound of a formula II as shown in the specification. By adopting the method disclosed by the invention, the raw materials are variable, a great amount of derivatives can be generated, the catalyst is cheap and easy to obtain, the cost can be greatly lowered, and no pollution can be caused; oxygen sources used in the method are water and Selectfluor; the reaction condition is gentle, and energy consumption can be reduced; in addition, the method has the characteristics of being high in yield, good in substrate universality, simple and convenient in aftertreatment operation, and the like.

Ir-catalyzed arylation, alkylation of quinones with boronic acids through C-C coupling

Ir-catalyzed arylation, alkylation of quinones with boronic acids was developed under room temperature. Both aryl and alkyl boronic acids are suitable for this transformation. This expands the application scope of the iridium catalyst. This is also an excellent proof that iridium catalysts can be used in the C-C coupling of quinones and naphthoquinones with alkyl boronic acids.

Synthesis of aryl substituted quinones as β-secretase inhibitors: Ligand-free direct arylation of quinones with aryl halides

The simple ligand-free direct arylation of quinones with aryl halides applying Pd(OAc)2as a catalyst in accordance with Heck reaction was studied. This reaction provided a simple and efficient synthetic approach to efficient inhibitors of β-secretase aryl-substituted quinones.

Transition metal-free direct C-H functionalization of quinones and naphthoquinones with diaryliodonium salts: Synthesis of aryl naphthoquinones as β-secretase inhibitors

A novel ligand-free, transition metal-free direct C.H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided an effective and easy way to synthesize β-secretase inhibitors. The radical trapping experiments showed that this progress was the radical mechanism.