Investigation of sp2-sp Coupling for Electron-Enriched Aryl Dihalides under Oxygen-Free Sonogashira Coupling Reaction Conditions Using a Two-Chamber Reaction System

9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[b]quinolizinium derivatives under relatively mild reaction conditions. The 9-(N,N-dimethylaminophenylethynyl)benzo[b]quinolizinium is only very weakly emitting, but the emission intensity increases by a factor >200 upon protonation, so that this derivative may operate as pH-sensitive light-up probe. Photometric and fluorimetric titrations of duplex and quadruplex DNA to 9-(arylethynyl)benzo[b]quinolizinium derivatives revealed a significant binding affinity of these compounds towards both DNA forms with binding constants ofKb= 0.2–2.2 × 105M−1.

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Synthesise of (4-Ethynyl-Phenyl)-(4-trifluoromethyl-phenyl)-Diazene, a Novel Intermediate of Azobenzene Liquid Crystal with High Birefrigence

Applied Mechanics and Materials ◽

10.4028/www.scientific.net/amm.584-586.1705 ◽

2014 ◽

Vol 584-586 ◽

pp. 1705-1708

Author(s):

Xiao Ping Huo ◽

Qi Pei Xu ◽

Zong Cheng Miao

Keyword(s):

Liquid Crystal ◽

Raw Materials ◽

Coupling Reaction ◽

Sonogashira Coupling ◽

Target Compound ◽

Reaction Conditions ◽

Silyl Group ◽

Sonogashira Coupling Reaction ◽

Optimum Reaction ◽

Ft Ir

In order to obtain an important azobenzene liquid crystal intermediate with phenylacetylene group, Sonogashira coupling reaction was used to preparation the compound. In this paper, the intermediate was synthesized by (4-Iodo-phenyl)-(4-trifluoromethyl-phenyl)-diazene and trimethyl silyl acetylene (TMSA) as raw materials, and then the trimethyl silyl group was removaled under the action of K2CO3. During the synthesis, the optimum reaction conditions were obtained, that the mol ratio of (4-Iodo-phenyl)-(4-trifluoromethyl-phenyl)-diazene and trimethyl silyl acetylene was 1:2, the reaction temperature was 80 oC. Fourier transform infrared spectroscopy (FT-IR) was used to measure the molecular structure of the target compound.

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Preparation of Novel Liquid Crystal Material with Trifluoromethyl Substitutent

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.785-786.690 ◽

2013 ◽

Vol 785-786 ◽

pp. 690-692

Author(s):

Yong Ming Zhang ◽

Yi Wei Wang ◽

Mei Zhang ◽

Jian Fang Liu ◽

Jie Si ◽

...

Keyword(s):

Liquid Crystal ◽

Coupling Reaction ◽

Sonogashira Coupling ◽

Reaction Conditions ◽

H Nmr ◽

Crystal Material ◽

Liquid Crystal Material ◽

Display Area ◽

Sonogashira Coupling Reaction ◽

Ft Ir

The liquid crystal material with trifluoromethyl substitutent is a very important liquid crystal monomer to combine mixture in the application of display area. In this paper, a kind of liquid crystal material with trifluoromethyl substitutent was synthesized by traditional method of Sonogashira coupling reaction, the reaction mechanism and reaction conditions were then obtained. In addition, the synthesized compound was characterized by FT-IR and1H-NMR to confirm the consistent structure with target compound.

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Synthesis of LC Intermediate Containing Trimethyl Silyl Acetylene Group

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.781-784.280 ◽

2013 ◽

Vol 781-784 ◽

pp. 280-282

Author(s):

Zong Cheng Miao ◽

Yi Wei Wang ◽

Yuan Yuan Li ◽

Lei Zhang ◽

Xin Zhang ◽

...

Keyword(s):

Liquid Crystal ◽

Reaction Time ◽

Reaction Temperature ◽

Raw Materials ◽

Coupling Reaction ◽

Sonogashira Coupling ◽

Reaction Conditions ◽

Sonogashira Coupling Reaction ◽

Acetylene Group ◽

Optimum Reaction

In order to obtain the important liquid crystal intermediate with trifluoromethyl substitutent, Sonogashira coupling reaction was used to synthesize the compound. In this paper, the intermediate was synthesized by 4'-Iodo-4-pentyl-biphenyl and trimethyl silyl acetylene (TMSA) as raw materials. During the synthesis, the optimum reaction conditions were obtained, that the mol ratio of 4'-Iodo-4-pentyl-biphenyl and trimethyl silyl acetylene is 1:2, the reaction temperature is 30 oC, and the reaction time is 10 h.

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Synthesis of Internal Alkynes through an Effective Tandem Elimination–Hydrodebromination–Cross-Coupling of gem-Dibromoalkenes with Halobenzenes

Synlett ◽

10.1055/s-0036-1590907 ◽

2017 ◽

Vol 29 (02) ◽

pp. 209-214 ◽

Cited By ~ 3

Author(s):

Yuan Ji ◽

Ning Zhong ◽

Zinan Kang ◽

Guobing Yan ◽

Ming Zhao

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Sonogashira Coupling ◽

Reaction Conditions ◽

One Pot ◽

Cross Coupling Reaction ◽

Sonogashira Coupling Reaction ◽

Palladium Catalyzed ◽

Internal Alkyne

Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

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