The copper-catalyzed synthesis of (<i>Z</i>)-2<i>H</i>-naphtho[1,8-<i>bc</i>]thiophenes with solid emission
Yuan Zhang, Weiping Lai, Lianpeng Zhang, Xiaoxing Gao, Guanyinsheng Qiu, Hongwei Zhou
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.