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Process for the preparation of polycyclic aromatic compounds substituted with aryl groups

A technology for polycyclic aromatic compounds, which is applied in the field of preparation of polycyclic aromatic compounds substituted with aryl groups, and can solve the problem of few reported cases

Inactive Publication Date: 2016-08-17
NAGOYA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, among the applicable substrates for direct arylation reported so far, most have heteroaromatic rings and positioning groups, and there are few reported cases of direct arylation of PAH (Non-Patent Document 3)

Method used

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  • Process for the preparation of polycyclic aromatic compounds substituted with aryl groups
  • Process for the preparation of polycyclic aromatic compounds substituted with aryl groups
  • Process for the preparation of polycyclic aromatic compounds substituted with aryl groups

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preparation example Construction

[0126] In the method for preparing an aromatic compound in the first aspect of the present invention, in the presence of a palladium compound and o-tetrachlorobenzoquinone, a polycyclic aromatic compound is reacted with a boron compound containing an aryl group that may have a substituent to obtain at least A polycyclic aromatic compound in which an aryl group may have a substituent.

[0127] [1-1] Polycyclic aromatic compounds

[0128] In the present invention, it is preferable to react by the following formula,

[0129] [Chemical formula 24]

[0130]

[0131] Where R 2 ~R 5 The same or different, each is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, especially 1 to 6; Ar is an optionally substituted aryl group having 6 to 50 carbon atoms; n is an integer of 1 to 4, Ar may be bonded to any cyclic structure and satisfy any one of the following requirements (1) to (4).

[0132] (1) R 2 ~R 5 All are hydrogen atoms.

[0133] (2) R 2 And R 5 Are all hydrogen atoms; R 3 Wit...

Embodiment 1～6

[0536] In Examples 1 to 6, phenylated pyrene was obtained by using the reaction formula shown in the following formula.

[0537] [Chemical formula 104]

[0538]

[0539] In detail, it is as follows.

Embodiment 1

[0541] Pd(OAc) 2 Solution (1.1mg, 5.0μmol, 2.5mol%), o-tetrachlorobenzoquinone (49mg, 0.20mmol, 1 equivalent), pyrene represented by the following formula (40mg, 0.20mmol, 1 equivalent), and

[0542] [Chemical formula 105]

[0543]

[0544] Phenylboronic acid (0.40 mmol, 2 equivalents) represented by the following formula was put into 1,2-dichloroethane (1,2-DCE, 2.0 mL), and stirred at 80°C for 2 hours.

[0545] [Chemical formula 106]

[0546] (Ph is phenyl)

[0547] The GC yield was measured using n-dodecane as an internal standard.

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Abstract

By using a palladium compound, o-chlorobenzoquinone and a specific boron compound, C-H / C-B coupling is performed to obtain a compound in which the C-H bond of PAH is directly arylated at the desired position by a simple method. In addition, if the substrate and boron compound are properly selected, and then undergo a ring condensation reaction, a large PAH can be further obtained. Furthermore, by using palladium compounds, o-chlorobenzoquinone and specific aromatic compounds to carry out C-H / C-H cross-coupling, the C-H bond of PAH can also be directly obtained at the desired position by a simple method. Arylated compounds. In addition, in this case too, if a substrate and a specific aromatic compound are appropriately selected, and then subjected to a ring condensation reaction, a further large PAH can be obtained.

Description

Technical field [0001] The invention relates to a method for preparing polycyclic aromatic compounds substituted with aryl groups. Background technique [0002] The two-dimensional sheet-like graphene with sp2 bonded carbon atoms has attracted attention in almost the entire field of science and technology. Since the shape and width determine the properties of graphene, the synthesis of graphene with a uniform structure is one of the most important topics in this research field. [0003] Regarding the application in the graphene, polycyclic aromatic compounds (PAH) are highly anticipated, and the potential demand for simple and effective synthesis methods of PHA derivatives is great. In addition, it can be considered that the direct arylation of the aromatic ring C-H bond using a transition metal catalyst is one of the simplest and ideal synthesis methods of PAH derivatives. From this point of view, the direct arylation of the C-H bond of commercially available small PAHs by a sim...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C2/86C07C5/44C07C15/20C07C15/30C07C15/38C07C17/263C07C22/08C07C25/22C07B61/00
CPCC07C43/21C07C2/86C07C17/263C07C2603/40C07C2603/50C07C2603/54C07C41/30C07C15/38C07C25/22C07C22/08C07C15/20C07C13/66C07C2/66C07C17/361
Inventor 伊丹健一郎望田宪嗣川澄克光濑川泰知梶野智敬
Owner NAGOYA UNIVERSITY
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