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

doi:10.6023/cjoc201603029

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

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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

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 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 Yibiao^a, Cheng Liang^a, Chen Lu^a, Li Bin^a, Sun Ning^b, Qing Ning^a

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 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).

1. One-Pot Synthesis of Substituted Thiophene and Furan Derivatives from Terminal Alkynes.PDF(1289KB)

Abstract

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

Cite this article

Li Yibiao, Cheng Liang, Chen Lu, Li Bin, Sun Ning, Qing Ning. One-Pot Synthesis of Substituted Thiophene and Furan Derivatives from Terminal Alkynes[J]. Chin. J. Org. Chem., 2016, 36(10): 2426-2436.

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基于末端炔烃一锅法合成取代噻吩和呋喃化合物

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

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