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Preparation method of Ir-O-P type catalyst diboric acid/ester compound

An ester compound and catalyst technology, applied in the field of organic synthesis, achieves the effects of strong designability, good compatibility and simple post-processing

Active Publication Date: 2022-01-28
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, limited by raw materials and methods, only diborides of arylhydrazone diborides and 2-phenylpyridine derivatives can be synthesized

Method used

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  • Preparation method of Ir-O-P type catalyst diboric acid/ester compound
  • Preparation method of Ir-O-P type catalyst diboric acid/ester compound
  • Preparation method of Ir-O-P type catalyst diboric acid/ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A kind of preparation method of Ir-O-P type catalyst diboronic acid / ester compound comprises the steps: under anhydrous and oxygen-free condition, organic boron source [B], β-N-aryl (alkane) substrate, metal iridium catalyst and The organic phosphine ligand is added into the organic solvent and reacted at 60-120° C. After the reaction is completed, the aryl (alkyl) diboronic acid / boric acid ester compound is obtained through post-treatment.

[0046] The structure of the organic boron source [B] is shown in formulas (I) to (IV):

[0047]

[0048] The structure of the β-N-aryl (alkane) base substrate is shown in formulas (IV) to (VII):

[0049]

[0050] The structure of described aryl (alkyl) base diboronic acid / boric acid ester compound is as shown in the formula:

[0051]

[0052] The molar ratio of the β-N-aryl(alkane)-based substrate to the organic boron source [B] is 1.0:1.0-4.0.

[0053] The reaction formula is as follows:

[0054]

[0055] After our st...

Embodiment 2

[0068] Add methoxycyclooctadiene iridium, triphenylphosphine, β-N-aryl (alkane) base substrate, bispinacol borate, organic solvent 2mL in the Schlenk tube of 10mL according to the raw material ratio of Table 1, React with heating and stirring at 60-120°C. After the reaction is completed according to the reaction conditions in Table 2, concentrate, mix the sample with silica gel, and purify by column chromatography to obtain the corresponding aryl (alkyl) diboronic acid / boric acid ester compound. The reaction process is as follows: Shown:

[0069]

[0070] Table 1

[0071]

[0072]

[0073]

[0074] The reaction conditions of the foregoing examples of table 2 and the resulting product

[0075]

[0076]

[0077]

[0078] In Table 2, T is the reaction temperature, and t is the reaction time.

[0079] Structural confirmation data of some compounds

[0080] The nuclear magnetic resonance (NMR) ( 1 H NMR and 13 C NMR) detection data are:

[0081]

[008...

Embodiment 3

[0096] The invention also discloses a water-resistant and oxygen-resistant Ir-O-P bond-containing novel metal iridium catalyst when preparing aryl (alkyl)-based diboronic acid / boric acid ester compounds, which can be widely used in various C-H bond boronations, substrates Good tolerance, catalytic activity is better than all kinds of commercially available metal iridium catalysts.

[0097] The beneficial effects of the present invention are:

[0098] 1. The preparation method of the Ir-O-P type catalyst diboronic acid / ester compound obtains the aryl (alkyl) base diboronic acid / boric acid ester compound through a one-pot method, which makes up for the need for multi-step synthesis of this type of compound and the limited range of substrates However, in the preparation of aryl triazene diborides, the target compound can be obtained in a higher yield even without adding a ligand. The high yield lays a good foundation for the application in the field of drug synthesis or material...

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Abstract

The invention discloses a preparation method of an Ir-O-P type catalyst diboronic acid / ester compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps that under the air condition, using an Ir metal complex and a phosphine ligand to form an active Ir-O-P type catalyst; and adding an organic boron source [B], a beta-N-aryl (alkyl) substrate and the Ir-O-P type catalyst into an organic solvent under anhydrous and anaerobic conditions, conducting reacting at 60-120 DEG C, and after the reaction is finished, performing post-treatment to obtain the aryl (alkyl) diboronic acid / borate compound. According to the reaction, the aryl (alkyl) diboronic acid / borate compound can be obtained through a one-pot method, and the limitation that the compound needs to be synthesized in multiple steps and the substrate range is limited is made up. In addition, in the preparation of the aryl triazene diboride, even if no ligand is added, a target compound can be obtained at a high yield, and based on the advantages, the method shows a very high yield after being expanded to a gram-level reaction, and lays a good foundation for application in the field of drug synthesis or material development.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to the research and development of a new Ir-O-P catalyst and its application in the preparation of aryl (alkyl) diboronic acid / boric acid ester compounds. Background technique [0002] Metal-catalyzed C–H bond activation is a rapidly developing new method in organic synthesis. The formation of C-B bond is one of the important forms of C-H bond activation. Due to the unique chemical properties of organoboron (borane, boric acid, borate ester), various forms of functional group transformation can be realized, which has important application value for the modification of drug structure and the development of new materials. [0003] In the prior art, limited by raw materials and methods, only arylhydrazone diborides and diborides of 2-phenylpyridine derivatives can be synthesized. Contents of the invention [0004] Aiming at the deficiencies of the prior art, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F15/00B01J31/24
CPCC07F5/025C07F15/0033B01J31/2404B01J2231/46B01J2531/827
Inventor 毛帅袁博张三奇陈艺铭赵亚浩王欣宇
Owner XI AN JIAOTONG UNIV
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