Organic Chemistry Portal



Transition-Metal-Free Method for the Synthesis of Benzo[b]thiophenes from o-Halovinylbenzenes and K2S via Direct SNAr-Type Reaction, Cyclization, and Dehydrogenation Process

Xiaoyun Zhang, Weilan Zeng, Yuan Yang, Hui Huang, Yun Liang*

*Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China, Email:

X. Zhang, W. Zeng, Y. Yang. H. Huang, Y. Liang, Synlett, 2013, 24, 1687-1688.

DOI: 10.1055/s-0033-1339289


A highly efficient synthesis of benzothiophenes from easily available o-halovinylbenzenes and potassium sulfide tolerates a wide range of functionalities and provides various 2-substituted benzo[b]thiophenes in high yields in the absence of a transition-metal catalyst.

see article for more examples


The reaction was not affected by the E:Z ratio of the substrate.

Yun Liang, October 8, 2014

Key Words

transition-metal-free, benzothiophenes, o-halovinylbenzenes, direct SNAr-type reaction, cyclization, dehydrogenation process

ID: J60-Y2013