Citation: 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]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2426-2436. doi: 10.6023/cjoc201603029 shu

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

Corresponding author: Li Yibiao, leeyib268@126.com
Received Date: 16 March 2016
Revised Date: 17 May 2016

Fund Project: Foundation for Distinguished Young Talents in Higher Education of Guangdong Province 2013LYM_0094Science Foundation for Young Teachers of Wuyi University 2015td01National Natural Science Foundation of China 21302146Natural Science Foundation of Guangdong Province S2013040012354

Figures(3)

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.
- one-pot synthesis,
- thiophene,
- furan,
- terminal alkyne
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