Copper(I)-Catalyzed Synthesis of 2,5-Disubstituted Furans and Thiophenes from Haloalkynes or 1,3-Diynes

Abstract

A regioselective synthesis of 2,5-disubstituted furans 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.

Synthesis of 2,5-diferrocenyl five-membered heterocyclic compounds and their electrochemistry

“…The possible reason of low yield could be ascribed to inefficient Pd(PPh 3 ) 3 Cl 2 catalyst. Higher yield (65-92%) could be obtained in similar reactions adopting gold or copper as catalysts [27,28]. Hence, the high yield synthetic method using 1,4-diferrocenyl-1,3-butadiyne as precursor to prepare furan derivatives would be studied through efficient catalysts in our future works.…”

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

“…However, the major drawback of this approach is the complex, time-consuming preparation of the complicated gold catalyst and the separate synthesis of the butadiyne substrates. In a similar study arylbutadiynes prepared by Glaser homocoupling were converted into symmetrical 2,5-di(hetero)arylfurans [32] employing the superbase system DMSO/KOH/H 2 O in the terminal cyclization step [33]. The same approach was applied to butadiynes that were formed by oxidative dimerization of arylalkynes with a Cu/Fe catalyst [34].…”

One-Pot Synthesis of Substituted Thiophene and Furan Derivatives from Terminal Alkynes

“…a Reaction conditions: unless otherwise noted, the reaction was carried out using terminal alkyne (1.2 mmol), iodobenzene (1 mmol 4,134.8,132.1,130.0,127.5,123.7,121.8,108.3;MS (EI,70 eV) 2,5-双(2-吡啶基)呋喃(3k) [11] : 淡黄色固体, 产率为 2-苯基苯并呋喃(5a): 淡黄色固体, 产率为 91%. m.p.…”