A kind of ruthenium-catalyzed method and application of cyclization reaction of dibenzyl ketone and internal alkyne to prepare polyaromatic substituted naphthalene derivatives
A technology of dibenzyl ketone and naphthalene derivatives, which is applied in the field of preparation of polyaromatic substituted naphthalene derivatives, can solve problems such as increasing production costs, and achieve the effect of simple and easy synthesis method
Active Publication Date: 2020-06-02
DALIAN UNIV
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Problems solved by technology
However, there are defects in this method. These reactions require a certain amount of ligand or an equivalent metal salt as an oxidant to complete the catalytic cycle, which not only increases the production cost, but also the metal salts are mostly heavy metal (copper, silver, etc.) salts that pollute the environment.
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Embodiment 1
[0016]
[0017] Add dibenzyl ketone (42 mg, 0.2 mmol), corresponding internal alkyne (0.1 mmol), catalyst [RuCl 2 (p-cymene)] 2 (9mg, 15% mol), 0.5mL toluene, then add dry sodium carbonate (21mg, 0.2mmol), potassium acetate (19mg, 0.2mmol), replace nitrogen three times, react at 100°C for 24 hours, then pass column chromatography Separation (eluent: petroleum ether) to obtain the target compound. Characterization is as follows.
[0018] 3-Benzyl-1-methyl-2-phenylnaphthalene: Yield: 40%. Melting point: 76-77°C. 1 H NMR (CDCl 3 ,400MHz)δ8.03(d,J=8.0Hz,1H),7.79(d,J=8.0Hz,1H),7.47-7.52(m,3H),7.33-7.36(m,3H),7.12-7.17 (m,3H),7.03-7.05(m,2H),6.88(d,J=6.8Hz,2H),3.83(s,2H),2.36(s,3H). 13 C NMR (CDCl 3 ,100MHz)δ141.0,140.9,140.1,137.4,132.8,132.1,129.7,129.1,128.2,128.1,128.1,126.7,126.5,125.7,125.6,125.6,124.4,40.8,16.6. 24 h 20 (M + ):308.1565,found:308.1563.
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The invention relates to a method for preparing polyaryl substituted naphthalene derivatives from dibenzyl ketone and endoacetylene cyclization reaction under catalytic action of ruthenium and application of the polyaryl substituted naphthalene derivatives. Cheap ruthenium ([RuCl2(p-cymene)]2) is used as a catalyst, dibenzyl ketone beta-H is activated to synthesize a hexatomic ring, namely the polyaryl substituted naphthalene derivatives are generated. In a reaction process, additives and oxidants are avoided, only alkalis are used simply, and reaction conditions are mild. The synthesis methodis simple, feasible, scientific, reasonable, environmentally friendly, economical, practical and suitable for large-scale production.
Description
technical field [0001] The invention relates to the fields of medical technology and photoelectric materials, and mainly relates to a preparation method and application of polyaromatic substituted naphthalene derivatives. Background technique [0002] Due to their unique electrochemical and photochemical properties and their application in n-conjugated functional materials, polyaromatic substituted naphthalene derivatives are more and more widely used in organic fluorescent materials, semiconductor materials, etc., and polyaromatic substitution Naphthalene derivatives also have important applications in drug synthesis. The preparation method adopted in the prior art has made a great breakthrough compared with the relatively harsh conditions of the previous cyclometallation, aryl halide, aryl acid and the like. At present, under mild conditions, polyaromatic substituted naphthalene derivatives are prepared by the cyclization reaction of the C-H bond (even double C-H bond) of...
Claims
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IPC IPC(8): C07C15/24C07C2/86C07C51/00C07C65/105C07C2/00C07C13/66C09K11/06
CPCC07C2/00C07C2/867C07C15/24C07C51/00C09K11/06C09K2211/1007C09K2211/1011C07C65/105C07C13/66
Inventor 张殊佳高杰
Owner DALIAN UNIV