Copper(I)-Catalyzed Synthesis of 2,5-Disubstituted Furans and Thiophenes from Haloalkynes or 1,3-Diynes
作者:Huanfeng Jiang、Wei Zeng、Yibiao Li、Wanqing Wu、Liangbing Huang、Wei Fu
DOI:10.1021/jo300692d
日期:2012.6.1
A regioselective synthesis of 2,5-disubstitutedfurans using copper(I) catalyst from haloalkynes in a one-pot procedure has been reported. This chemistry proceeds through the hydration reaction of 1,3-diynes, which can be readily prepared from the coupling reaction of haloalkynes in the presence of CuI. The procedure also can be used for the facile synthesis of 2,5-disubstituted thiophenes.
A one-pot tandem Wittig/conjugate reduction/PaalKnorr reaction is reported for the synthesis of di- or trisubstituted furans. This novel sequence first demonstrates the possibility of successively recycling waste from upstream steps to catalyze downstream reactions.