Diaryl compound and preparation method thereof

A compound, biaryl technology, applied in the field of organic synthesis, can solve problems such as application limitations

Inactive Publication Date: 2012-08-15
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The substrates in the reaction are limited to polyfluorinated aryl carboxylic acids, which greatly limits the application

Method used

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  • Diaryl compound and preparation method thereof
  • Diaryl compound and preparation method thereof
  • Diaryl compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]

[0045] Under the reaction conditions of nitrogen gas, Pd(OAc) was successively loaded into the reaction flask 2 (4mol%, 0.9mg), PPh 3 (8mol%, 2.1mg), compound 1a (0.1mmol, 30mg), K 2 CO 3 (0.12mmol, 17mg), solvent N-methylpyrrolidone (0.5mL). Then the system was stirred in the air at 75°C for about 12 hours, and the reaction was quenched by adding HCl (1N, 5mL), extracted with ethyl acetate (15mL×3), then dried with anhydrous sodium sulfate, and then washed with 100- Adsorbed on 200-mesh silica gel, and then washed through a 300-400-mesh silica gel column to obtain product 2a with a yield of 96%. oily liquid; 1 H NMR (400MHz, CDCl 3)δ5.02(s, 2H), 6.91(dd, J=8.1, 1.2Hz, 1H), 6.96(dt, J=7.5, 1.2Hz, 1H), 7.05(d, J=7.4Hz, 1H), 7.12-7.20(m, 2H), 7.28(t, J=7.6Hz, 1H), 7.60(d, J=7.7Hz, 1H), 7.64(dd, J=7.7, 1.6Hz, 1H); IR(KBr ): 3179, 1484, 1400, 1244, 1120, 1017, 755, 688cm -1 ; MS (EI) m / z: 182 (M + ), 181, 152, 127, 115, 91, 76. The above data prove that the t...

Embodiment 2

[0047]

[0048] Under the reaction conditions of nitrogen gas, Pd(OAc) was successively loaded into the reaction flask 2 (4mol%, 0.9mg), PPh 3 (8mol%, 2.1mg), compound 1b (0.1mmol, 32mg), K 2 CO 3 (0.12mmol, 17mg), solvent N-methylpyrrolidone (0.5mL). Then the system was stirred in the air at 75°C for about 12 hours, and the reaction was quenched by adding HCl (1N, 5mL), extracted with ethyl acetate (15mL×3), then dried with anhydrous sodium sulfate, and then washed with 100- Adsorbed on 200-mesh silica gel, and then washed through a 300-400-mesh silica gel column to obtain product 2b with a yield of 99%. oily liquid; 1 H NMR (400MHz, CDCl 3 )δ2.41(s, 3H), 5.12(s, 2H), 6.94(d, J=8.2Hz, 1H), 7.09(dd, J=8.2, 1.6Hz, 1H), 7.18(d, J=7.5 Hz, 1H), 7.31(dt, J=7.5, 1.1Hz, 1H), 7.41(t, J=7.6, 7.6Hz, 1H), 7.58(d, J=1.6Hz, 1H), 7.73(d, J =7.7Hz, 1H); IR (KBr): 3030, 2960, 2920, 2842, 1497, 1250, 816, 770cm -1 ; MS (EI) m / z: 197 (M + ), 196, 195, 181, 165, 139, 115, 97. The ab...

Embodiment 3

[0050]

[0051] Under the reaction conditions of nitrogen gas, Pd(OAc) was successively loaded into the reaction flask 2 (4mol%, 0.9mg), PPh 3 (8mol%, 2.1mg), compound 1c (0.1mmol, 32mg), K 2 CO 3 (0.12mmol, 17mg), solvent N-methylpyrrolidone (0.5mL). Then the system was stirred in the air at 75°C for about 12 hours, and the reaction was quenched by adding HCl (1N, 5mL), extracted with ethyl acetate (15mL×3), then dried with anhydrous sodium sulfate, and then washed with 100- Adsorbed on 200-mesh silica gel, and then washed through a 300-400-mesh silica gel column to obtain product 2c with a yield of 92%. oily liquid; 1 H NMR (400MHz, CDCl 3 )δ2.34(s, 3H), 5.09(s, 2H), 6.81(s, 1H), 6.87(d, J=7.8Hz, 1H), 7.12(d, J=7.4Hz, 1H), 7.22- 7.26(m, 1H), 7.35(t, J=7.6Hz, 1H), 7.61(d, J=7.9Hz, 1H), 7.65(d, J=7.7Hz, 1H); IR(KBr): 3026, 2965, 2844, 1618, 1492, 1158, 1030, 770cm -1 ; MS (EI) m / z: 197 (M + ), 196, 195, 181, 165, 139, 115, 97. The above data prove that the target ...

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Abstract

The invention relates to a diaryl compound and a preparation method thereof, particularly a method for intramolecularly coupling aryl carboxylic acid or carboxylate with aryl bromide. The invention implements intramolecular decarboxylation or degreasing and coupling reaction with aryl bromide under mild conditions (70-120 DEG C), thereby forming multiple diaryl compounds in different structures.

Description

technical field [0001] The invention belongs to the field of organic synthesis, specifically relates to a biaryl compound and a preparation method thereof, and more specifically relates to a method for coupling an intramolecular aryl carboxylic acid or carboxylic acid ester with an aryl halide. Background technique [0002] Biaryl fragments exist in a large number of bioactive molecules and are very important and valuable structures. Biaryl compounds are important structural units widely present in natural products and drug molecules. Among many organic synthesis methods, the most effective method for constructing biaryl compounds is transition metal-catalyzed cross-coupling reaction. Recently, transition metal-catalyzed decarboxylation coupling reactions have been rapidly developed. At present, the synthesis of biaryl compounds mainly contains the following synthetic methods: [0003] 1. Palladium-catalyzed coupling of arylboronic acid and aryl halide, which is the famou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/10C07D311/80C07D311/78C07D307/91C07D221/12C07D209/86C07D487/04
Inventor 沈增明倪振杰莫松王静主亚敏
Owner SHANGHAI JIAO TONG UNIV
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