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Updated: Nov 18, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
The copper-catalyzed synthesis of (Z)-2H-naphtho[1,8-bc]thiophenes with solid emission
Yuan Zhang1, Weiping Lai1, Lianpeng Zhang2
1College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China. lpz@zju.edu.cn.
Abstract:
In recent years, one of the main research interests of our group has been the construction of 6/5 π-systems through the regioselective conversion of parallel alkynes in naphthalene with the aim of exploiting potential fluorescent materials. Herein, the copper-catalyzed synthesis of polysubstituted (Z)-2H-naphtho[1,8-bc]thiophenes from 8-halo-1-ethynylnaphthalenes using potassium ethylxanthate as the sulfur source is reported. In this protocol, a series of thiophene-fused 6/5 π-system compounds was synthesized via copper-catalyzed Ullmann-type C(aryl)-S bond formation and the α-addition of an alkyne bond with high selectivity and in high yields. The synthesized polysubstituted (Z)-2H-naphtho[1,8-bc]thiophenes exhibited solid emission, which made them potential candidates for use in optoelectronic conjugated materials. By using DMSO/D2O (3 : 1) as the reaction solvent, the deuterated products could be obtained in good yields under standard conditions.
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