Synthetic method of dibenzoselenophene compound

A technology of dibenzoselenophene and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of low yield of target product, harsh reaction conditions, complexity, etc., and achieve good functional group compatibility, wide substrate range, and no metal participation Effect

Active Publication Date: 2020-12-04
WENZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the prior art discloses a variety of synthetic approaches represented by the above, in these methods, it is extremely difficult and expensive to obtain the reaction raw materials, and the use of expensive catalytic reaction systems, harsh reaction conditions and comp

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  • Synthetic method of dibenzoselenophene compound
  • Synthetic method of dibenzoselenophene compound
  • Synthetic method of dibenzoselenophene compound

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Experimental program
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Embodiment 1-10

[0021] Embodiment 1-10 Reaction condition optimization embodiment

[0022] Using [1,1'-biphenyl]-2-ylboronic acid represented by formula 1a as the template substrate, the optimal reaction conditions were screened. The reaction formula is as follows:

[0023]

Embodiment 1

[0025] [1,1'-biphenyl]-2-ylboronic acid (0.2mmol), Se (0.6mmol) and DMSO (2ml) shown in Formula 1a were loaded into a 25mL Schlenk tube equipped with a stirring bar, and the reaction mixture Stir at 140° C. for 24 h under an air atmosphere, take a sample and detect no reaction by TLC and / or GC-MS.

Embodiment 2

[0027] [1,1'-biphenyl]-2-ylboronic acid (0.2mmol), TMSCN (1mol%, ie 0.002mmol), Se (3 eq. , ie 0.6mmol) and DMSO (2ml). The reaction mixture was stirred at 140° C. for 24 h under an air atmosphere. After cooling, the reaction mixture was diluted with 10 mL of ether, filtered through a pad of silica gel and concentrated under reduced pressure. Then the residue was purified by silica gel flash chromatography to obtain the target product phenoxeselene / phenothioselenium represented by formula 1d with a yield of 40%. white solid; 1 H NMR (500MHz, CDCl 3 )δ8.24-8.23(m,2H),8.06-8.04(m,2H),7.62-7.59(m,2H),7.56-7.53(m,2H); 13 C NMR (125MHz, CDCl 3 )δ 139.6, 138.5, 127.1, 126.3, 125.1, 123.1.

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Abstract

The invention discloses a synthetic method for preparing a dibenzoselenophene compound. According to the method, a C-Se bond is formed through free radical cyclization of a biaryl boric acid substratecatalyzed by TMSCN and selenium powder, so that the dibenzoselenophene compound is constructed. The new strategy has the advantages of no metal participation, no additive promotion, wide substrate range, good functional group compatibility, simple operation, high yield and the like.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of dibenzoselenophene compounds. Background technique [0002] Selenophene derivatives have attracted widespread attention in fields such as organic synthetic chemistry, materials science, and organic optoelectronic devices. Especially in the field of optoelectronic devices, they have shown good performance and have become a new research hotspot in the field of optoelectronic materials. However, due to the difficulty in the source of selenophene derivatives and the harsh conditions of the preparation process, the research on the preparation of selenophene derivatives makes the development of selenophene chemistry relatively slow, which greatly affects the rapid development of selenophene chemistry (the preparation of selenophene derivatives and Progress in Applied Research, Li Chunli et al., "Journal of Henan University (Natural Science ...

Claims

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Application Information

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IPC IPC(8): C07D345/00
CPCC07D345/00
Inventor 周云兵李金承刘妙昌吴华悦
Owner WENZHOU UNIVERSITY
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