Citation: Peng Lifen, Jiang Juan, Peng Chao, Dai Ningning, Tang Zilong, Jiao Yinchun, Chen Jinyang, Xu Xinhua. Synthesis of Unsymmetrical Aromatic Acetylenes by Diphenyl Chlorophosphate-Promoted Condensation Reaction of Aromatic Aldehydes and Sulfones[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 3013-3018. doi: 10.6023/cjoc201704053 shu

Synthesis of Unsymmetrical Aromatic Acetylenes by Diphenyl Chlorophosphate-Promoted Condensation Reaction of Aromatic Aldehydes and Sulfones

a.
Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201
b.
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Corresponding author: Peng Lifen, 1060137@hnust.edu.cn Xu Xinhua, xhx1581@hnu.edu.cn
Received Date: 30 April 2017
Revised Date: 24 July 2017
Available Online: 16 November 2017
Fund Project: the Doctoral Foundation of Hunan University of Science and Technology E51693the National Natural Science Foundation of China 21402048the General Project of Hunan Education Department 17C0629Project supported by the General Project of Hunan Education Department (No. 17C0629), the Doctoral Foundation of Hunan University of Science and Technology (No. E51693), the Open Foundation of Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology (No. E21630), the National Natural Science Foundation of China (No. 21402048)the Open Foundation of Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology E21630

Figures(1)

Diphenyl chlorophosphate-promoted condensation reaction of aromatic aldehydes and sulfones, proceeding at room temperature, could been applied to synthesize unsymmetrical aromatic acetylenes. It was found that functional groups on aromatic ring of aldehydes and sulfones had little effect on the reaction. A series of unsymmetrical diphenyl, thienyl, pyridyl, coumarin and diphenylphosphoryl aromatic acetylenes were prepared by the reaction. Based on the molecular structure, the reason why this reaction could proceed at room temperature is explained The reaction showed some outstanding features including simple operation, wide functional group tolerance, high yields and mild reaction conditions.
- condensation reaction,
- unsymmetrical aromatic acetylene,
- coumarin acetylene,
- diphenylphosphoryl aromatic acetylene
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