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Method for preparing coupling product through visible light catalysis cross dehydrogenation coupling

A technology of cross-dehydrogenation coupling and visible light, which is applied in organic chemical methods, chemical instruments and methods, chemical/physical processes, etc., to achieve the effects of small loading, improved reaction selectivity, and simple process

Active Publication Date: 2015-07-15
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there has been no report on the use of platinum complexes as visible light catalysts to achieve CDC reactions.

Method used

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  • Method for preparing coupling product through visible light catalysis cross dehydrogenation coupling
  • Method for preparing coupling product through visible light catalysis cross dehydrogenation coupling
  • Method for preparing coupling product through visible light catalysis cross dehydrogenation coupling

Examples

Experimental program
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Effect test

Embodiment 1

[0050] A method for preparing a coupled product through visible light catalyzed cross dehydrogenation coupling, comprising the following steps:

[0051] With 6-phenyl 2,2'-bipyridine divalent platinum complex (R 10 for C 6 h 4 CH 3 -4, R 11 for PPh 3 , R 12 , R 13 H) is a visible light catalyst, add 0.87mg of the catalyst to 1mL of acetonitrile; take 0.1mmol of N-phenyl-1,2,3,4-tetrahydroisoquinoline (X, Y is H), and 0.2mmol of indole (R 1 , R 2 , R 3 , R 4 , R 5 For H) dissolved in 1mL acetonitrile; 1mL catalyst solution and 1mL reactant solution to obtain 2mL mixed solution, wherein the concentration of visible light catalyst is 5.0×10 -4 M; then use 450nm ± 10nm Blue LEDs to illuminate in the air environment at 40°C for 10h, TLC to monitor the reaction, after the reaction, add ethyl acetate to extract, wash with saturated saline, dry with anhydrous sodium sulfate, and finally pass through the column separate. H NMR, C NMR, and mass spectrometry identified the ...

Embodiment 2

[0053] A method for preparing a coupled product through visible light catalyzed cross dehydrogenation coupling, comprising the following steps:

[0054] With 6-phenyl 2,2'-bipyridine divalent platinum complex (R 10 for C 6 h 4 CH 3 -4, R 11 for PPh 3 , R 12 , R 13 is H) is a visible light catalyst, 0.87mg of the catalyst is added to 1mL of water; 0.1mmol of N-phenyl-1,2,3,4-tetrahydroisoquinoline (X, Y is H), and 0.2mmol of indole ( R 1 , R 2 , R 3 , R 4 , R 5 For H), add 1mL water; mix 1mL catalyst solution and 1mL reactant solution to get 2mL mixed solution, in which the concentration of visible light catalyst is 5.0×10 -4 M; then use 450nm ± 10nm Blue LEDs to illuminate in the air environment at 40°C for 10h, TLC to monitor the reaction, after the reaction, add ethyl acetate to extract, wash with saturated saline, dry with anhydrous sodium sulfate, and finally pass through the column separate. H NMR, C NMR, and mass spectrometry identified the product as 1-(1H...

Embodiment 3

[0056] A method for preparing a coupled product through visible light catalyzed cross dehydrogenation coupling, comprising the following steps:

[0057] With 6-phenyl 2,2'-bipyridine divalent platinum complex (R 10 for C 6 h 4 CH 3 -4, R 11 for PPh 3 , R 12 , R 13 H) is a visible light catalyst, add 0.87mg of the catalyst to 1mL DMF; take 0.1mmol N-phenyl-1,2,3,4-tetrahydroisoquinoline (X, Y are H), and 0.2mmol indole (R 1 , R 2 , R 3 , R 4 , R 5 For H) dissolved in 1 mL of DMF; 1 mL of catalyst solution and 1 mL of reactant solution were obtained to obtain 2 mL of mixed solution, in which the concentration of visible light catalyst was 5.0×10 -4 M; then use 450nm ± 10nm Blue LEDs to illuminate in the air environment at 40°C for 10h, TLC to monitor the reaction, after the reaction, add ethyl acetate to extract, wash with saturated saline, dry with anhydrous sodium sulfate, and finally pass through the column separate. H NMR, C NMR, and mass spectrometry identifie...

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Abstract

The invention discloses a method for preparing a coupling product through visible light catalysis cross dehydrogenation coupling. In the catalysis reaction, a polypyridine platinum complex is used as a photocatalyst; and under visible light irradiation in the air environment, a cross coupling reaction can be performed between tertiary amine and a nucleophile to obtain the coupling product. According to the method, the platinum complex is used as a visible light catalyst to realize an aerobic cross dehydrogenation coupling reaction; the whole process is simple and efficient; and the reaction conditions are very mild.

Description

technical field [0001] The invention belongs to the technical field of catalytic synthesis, and relates to a method for preparing coupling products through visible light catalytic cross-dehydrogenation coupling. Background technique [0002] Cross-dehydrogenation coupling reaction (CDC) is to directly couple different carbon-hydrogen bonds to form new carbon-carbon bonds without preactivating the reactants, which is very consistent with green chemistry and "atom economy" reactions It has become a hot spot in organic reaction methodology in recent years. The general formula for the cross dehydrogenation coupling reaction is: [0003] [0004] In cross-dehydrocoupling reactions, it is usually necessary to add metal catalysts to activate substrates or stabilize reaction intermediates. For example, Shun-Ichi Murahashi’s group can undergo cross-dehydrogenation coupling reaction with hydrocyanic acid under the catalysis of ruthenium trichloride in an oxygen atmosphere to gene...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07D401/04C07D217/14B01J31/28B01J31/22
Inventor 吴骊珠钟建基孟庆元
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI