Copper catalyst system for decarboxylation coupling reaction
A copper catalyst, decarboxylation coupling technology, applied in physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, organic chemistry, etc., can solve problems such as palladium product residue, application impact, toxicity, etc., to achieve Cost reduction, environmental protection, high selectivity effect
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Examples
Embodiment 1
[0027] Cinnamic acid (0.5mmol), CuO (0.05mmol), and toluene (2mL) were sequentially loaded into a pressure-resistant Schlenk test tube, and the system was evacuated and replaced with argon three times. Di-tert-butyl peroxide (1mmol) was added to the device, and then the system was sealed and heated in an oil bath at 110°C for about 24 hours. After the reaction was completed, the solvent was distilled off, and after concentration, it was concentrated and passed through simple column chromatography (petroleum ether was used as the eluent). (60-90° C.)) to obtain the decarboxylation coupling product (3-phenyl-propenyl)-benzene (89.4 mg), with a yield of 92%. Its NMR data are: 1 H NMR (300MHz, CDCl 3 ) (δ, ppm) 7.40-7.28 (m, 6H), 7.26-7.15 (m, 3H), 6.46 (d, J=15.9Hz, 1H), 6.40-6.30 (m, 1H), 3.55 (d, J = 6.2Hz, 2H); 13 C NMR (75MHz, CDCl 3)(δ, ppm) 140.6, 137.9, 131.5, 129.7, 129.2, 129.1, 129.0, 127.6, 126.6, 126.6, 39.8; high-resolution mass spectrometry data are: HRMS calcd ...
Embodiment 2
[0029] 4-Chlorocinnamic acid (0.5mmol), CuO (0.05mmol), and toluene (2mL) were sequentially loaded into a pressure-resistant Schlenk test tube, and the system was evacuated and replaced with argon three times under gas protection. Di-tert-butyl peroxide (1mmol) was added into the micro-injector, and then the system was sealed and heated in an oil bath at 110°C for about 24 hours. The decarboxylation coupling product 1-chloro-4-(3-phenyl-propenyl)-benzene (101.8 mg) can be obtained by using petroleum ether (60-90° C.) with a yield of 89%. Its NMR data are: 1 H NMR (300MHz, CDCl 3 ) (δ, ppm) 7.35-7.28 (m, 2H), 7.23 (d, J = 10.2Hz, 6H), 6.44-6.26 (m, 2H), 3.53 (d, J = 5.6Hz, 2H); 13 C NMR (100MHz, CDCl 3 )(δ, ppm) 140.0, 136.1, 132.8, 130.2, 123.0, 128.8, 128.8, 128.7, 127.5, 126.4, 39.5; high-resolution mass spectrometry data is: HRMS calcd.for[C 15 h 13 Cl] + requires m / z 228.0706, found 228.0705.
Embodiment 3
[0031] 4-Fluorocinnamic acid (0.5mmol), CuO (0.05mmol), and toluene (2mL) were successively loaded into a pressure-resistant Schlenk test tube, and the system was evacuated and replaced with argon three times under gas protection. Di-tert-butyl peroxide (1mmol) was added into the micro-injector, and then the system was sealed and heated in an oil bath at 110°C for about 24 hours. The decarboxylation coupling product 1-fluoro-4-(3-phenyl-propenyl)-benzene (96.6 mg) can be obtained by using petroleum ether (60-90° C.) with a yield of 91%. Its NMR data are: 1 H NMR (300MHz, CDCl 3 ) (δ, ppm) 7.32-7.22 (m, 6Hz), 6.97 (t, J = 8.7Hz, 2H), 6.41 (d, J = 15.8Hz, 1H), 6.33-6.20 (m, 1H), 3.53 ( d, J=6.4Hz, 2H); 13 C NMR (101MHz, CDCl 3 )(δ, ppm) 162.5(d, 1 J=244.5Hz), 140.5, 134.1(d, 4 J=2.8Hz), 130.3, 129.5, 129.1 (d, 3 J=9.8Hz, ), 128.8, 128.0(d, 3 J=7.9Hz), 126.7, 115.9, (d, 2 J=21.4Hz), 39.8; The high-resolution mass spectrometry data is: HRMS calcd.for[C 15 h 13 F] + req...
PUM
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com