有机化学 ›› 2017, Vol. 37 ›› Issue (11): 3013-3018.DOI: 10.6023/cjoc201704053 上一篇    下一篇

研究简报

氯磷酸二苯酯介入的芳香醛与砜缩合制备非对称芳香炔烃

彭丽芬a, 蒋娟a, 彭超a, 代宁宁a, 唐子龙a, 焦银春a, 陈锦杨b, 许新华b   

  1. a 湖南科技大学理论有机化学与功能分子教育部重点实验室 精细聚合物可控制备及功能化应用湖南省重点实验室 湖南科技大学化学化工学院 湘潭 411201;
    b 湖南大学化学化工学院 化学生物传感与计量学国家重点实验室 长沙 410082
  • 收稿日期:2017-04-30 修回日期:2017-07-24 发布日期:2017-08-16
  • 通讯作者: 彭丽芬, 许新华 E-mail:1060137@hnust.edu.cn;xhx1581@hnu.edu.cn
  • 基金资助:

    湖南省教育厅一般项目(No.17C0629)、湖南科技大学博士启动基金(No.E51693)、湖南科技大学理论有机化学与功能分子教育部重点实验室开放基金(No.E21630)和国家自然科学基金(No.21402048)资助项目.

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

Peng Lifena, Jiang Juana, Peng Chaoa, Dai Ningninga, Tang Zilonga, Jiao Yinchuna, Chen Jinyangb, Xu Xinhuab   

  1. 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
  • Received:2017-04-30 Revised:2017-07-24 Published:2017-08-16
  • Contact: 10.6023/cjoc201704053 E-mail:1060137@hnust.edu.cn;xhx1581@hnu.edu.cn
  • Supported by:

    Project 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).

氯磷酸二苯酯促进芳香醛与砜缩合反应在室温下有效进行,能高收率形成对应的非对称芳香炔烃.考察了醛及砜芳环上取代基对反应的影响,结果表明不论是吸电子基还是给电子基对反应都无明显影响,制备了一系列官能团化的非对称二苯基炔烃、噻吩及吡啶类炔烃、香豆素类炔烃及二苯基膦酰基保护的二炔烃和三炔烃,并从分子结构上阐明了本缩合反应可在室温下有效进行的原理.

关键词: 缩合反应, 非对称芳香炔烃, 香豆素炔烃, 二苯基膦酰基炔烃

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.

Key words: condensation reaction, unsymmetrical aromatic acetylene, coumarin acetylene, diphenylphosphoryl aromatic acetylene