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Synthetic method of 4,6-di(diphenylphosphine)phenazine compound

A technology of diphenylphosphine and diphenylphosphinephenyl, which is applied in the synthesis of organic phosphine compounds and the synthesis of 4,6-diphenazine compounds, can solve the problems of harsh deprotection conditions and poor positioning effects, etc. Achieve the effects of avoiding deprotection, overcoming poor positioning effect, and mild reaction conditions

Active Publication Date: 2019-07-12
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantage of this method is that the protective groups used are mostly alkyl or phenethyl groups. On the one hand, the positioning effect is not good, and lithiation can also occur at the 1 and 9 positions of phenoxazine; on the other hand, the deprotection conditions are harsh. Requires palladium carbon catalytic hydrogenation conditions to remove

Method used

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  • Synthetic method of 4,6-di(diphenylphosphine)phenazine compound
  • Synthetic method of 4,6-di(diphenylphosphine)phenazine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Under the protection of argon, 700 mL of reaction solvent acetonitrile was added to the dry reactor, and then 538 g of bis(2-diphenylphosphinephenyl) ether (compound 2), 14 g of cuprous bromide, tert-butyl Hydrogen peroxide [(CH 3 ) 3 COOH] 180 g, aqueous solution of sodium azide 100 mL (130 g / 100 mL), 30 o Stirring and reacting at C for 12 h; adding [(RhCp*Cl 2 ) 2 ] 12 g, silver hexafluoroantimonate 34 g, 70 o C reaction for 18 h; after stopping the reaction, the reaction system was cooled to room temperature, extracted, dried, and recrystallized to obtain the target product 4,6-bis(diphenylphosphine)phenazine (compound 1) 468 g (yield 85%) . 1 H NMR (400 MHz, C 6 D. 6 ): δ 7.37 (m, 8H), 6.98 (m, 12H), 6.25 (m, 2H), 5.84 (d, 2H), 4.23 (s, 1H). 31 P{ 1 H}NMR (162 MHz, C 6 D. 6 ): δ -17.6. 13 C{ 1 H) NMR (100 MHz, C 6 D. 6 ): δ 145.9, 137.5, 134.2, 131.8, 128.5, 126.1, 125.7, 125.6, 113.5.

Embodiment 2

[0018] Under the protection of argon, 700 mL of reaction solvent acetonitrile was added to the dry reactor, and then 538 g of bis(2-diphenylphosphinephenyl) ether (compound 2), 14 g of cuprous bromide, tert-butyl Hydrogen peroxide [(CH 3 ) 3 COOH] 180 g, aqueous solution of sodium azide 100 mL (130 g / 100 mL), 30 o Stirring and reacting at C for 12 h; adding [(RhCp*Cl 2 ) 2 ] 12 g, silver hexafluoroantimonate 34 g, 100 o C reaction for 18 h; after stopping the reaction, the reaction system was cooled to room temperature, extracted, dried, and recrystallized to obtain 507 g of the target product 4,6-bis(diphenylphosphine)phenazine (compound 1) (92% yield) .

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Abstract

The invention discloses a synthetic method of a 4,6-di(diphenylphosphine)phenazine compound and belongs to the field of organic synthesis. In an anhydrous and oxygen-free atmosphere, bis(2-diphenylphosphinephenyl)ether is used as a raw material to react with sodium azide, and 4,6-di(diphenylphosphine)phenazine is synthesized through azidation / intramolecular C-H ammoniation. The synthetic method has advantages of few reaction steps, mild reaction condition, simple operation and high yield, greatly promoting the application of the compound in the field of catalysis.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a synthesis method of a class of organic phosphine compounds, in particular to a synthesis method of 4,6-bis(diphenylphosphine)phenazine compounds. [0002] technical background [0003] Coupling reactions involving organophosphine catalysts are effective means for forming bonds such as C-C, C-N, and C-S in organic synthesis, and are widely used in the synthesis of natural products, functional materials, drugs, liquid crystal molecules, and biologically active compounds. 4,6-bis(diphenylphosphine)phenazine is an important class of catalyst ligands, which can react with transition metal compounds to form homogeneous catalysts. It is widely used in the field of industrial catalysis, especially in coupling reactions in the field of organic synthesis . 4,6-bis(diphenylphosphine)phenazine compound has superior electronic effect and steric effect due to its special electron-rich property...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6533
CPCC07F9/65335
Inventor 刘婷婷陈辉李云飞赵顺伟周铎冯海东杨振强段征杨瑞娜
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD