Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2426-2436.DOI: 10.6023/cjoc201603029 Previous Articles     Next Articles

Articles

基于末端炔烃一锅法合成取代噻吩和呋喃化合物

李亦彪a, 程亮a, 陈路a, 李滨a, 孙宁b, 卿宁a   

  1. a 五邑大学化学与环境工程学院 江门 529020;
    b 江门职业技术学院材料技术系 江门 529020
  • 收稿日期:2016-03-16 修回日期:2016-05-17 出版日期:2016-10-25 发布日期:2016-06-08
  • 通讯作者: 李亦彪,卿宁,E-mail:leeyib268@126.com E-mail:leeyib268@126.com
  • 基金资助:

    国家自然科学基金(No.21302146)、广东省自然科学基金(No.S2013040012354)、广东高校优秀青年创新人才培养计划(No.2013LYM_0094)和五邑大学青年基金(No.2015td01)资助项目.

One-Pot Synthesis of Substituted Thiophene and Furan Derivatives from Terminal Alkynes

Li Yibiaoa, Cheng Lianga, Chen Lua, Li Bina, Sun Ningb, Qing Ninga   

  1. a School of Chemical & Environmental Engineering, Wuyi University, Jiangmen 529020;
    b Department of Material Technology, Jiangmen Polytechnic, Jiangmen 529020
  • Received:2016-03-16 Revised:2016-05-17 Online:2016-10-25 Published:2016-06-08
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21302146), the Natural Science Foundation of Guangdong Province (S2013040012354), the Foundation for Distinguished Young Talents in Higher Education of Guangdong Province (No.2013LYM_0094) and the Science Foundation for Young Teachers of Wuyi University (No.2015td01).

The development of efficient and sustainable methods for the synthesis of thiophene and furan derivatives is an important task because of the central role of this class of compounds in many natural products, pharmaceuticals and designed materials applications. In this work, a highly efficient selective synthesis of 2,5-disubstituted furan, 2,5-disubstituted thiophene derivatives, benzo[b]furan and benzo[b]thiophene derivatives using terminal alkynes has been developed. This one-pot procedure involves C(sp)-C(sp) oxidative coupling reaction, the selective hydration and intramolecular annulation of two C≡C triple bond which is a promising synthetic strategy. Meanwhile, the benzo[b]furan and benzo[b]thiophene derivatives were facilely synthesized via Sonogashira coupling reaction, regioselective C-F bond hydration and annulation process in good yield. This reaction was a convenient and simple pathway for the synthesis of the thiophene or furan derivatives.

Key words: one-pot synthesis, thiophene, furan, terminal alkyne