1644191-20-7Relevant academic research and scientific papers
Synthesis of furans through silver-catalyzed propargyl-claisen rearrangement followed by cyclocondensation
Palisse, Adeline,Kirsch, Stefan F.
, p. 7095 - 7098 (2015/01/09)
The generation of highly substituted furans from propargyl vinyl ethers bearing a free hydroxy group was investigated. In the presence of catalytic amounts of AgBF4, a formal [3,3] sigmatropic rearrangement takes place in the first stage of the
Gold-catalyzed C(sp3)-H/C(sp)-H coupling/cyclization/oxidative alkynylation sequence: A powerful strategy for the synthesis of 3-alkynyl polysubstituted furans
Ma, Yuanhong,Zhang, Shuai,Yang, Shiping,Song, Feijie,You, Jingsong
, p. 7870 - 7874 (2014/08/05)
In sharp contrast to the gold-catalyzed reactions of alkynes/allenes with nucleophiles, gold-catalyzed oxidative cross-couplings and especially C-H/C-H cross-coupling have been under represented. By taking advantage of the unique redox property and carbophilic π acidity of gold, this work realizes the first gold-catalyzed direct C(sp3)-H alkynylation of 1,3-dicarbonyl compounds with terminal alkynes under mild reaction conditions, with subsequent cyclization and in situ oxidative alkynylation. A variety of terminal alkynes including aryl, heteroaryl, alkenyl, alkynyl, alkyl, and cyclopropyl alkynes all successfully participate in the domino reaction. The protocol offers a simple and region-defined approach to 3-alkynyl polysubstituted furans. Pure and simple: The first gold-catalyzed C(sp3)-H/C(sp)-H cross-coupling/cyclization/oxidative alkynylation sequence of 1,3-dicarbonyl compounds reacting with terminal alkynes has been achieved under mild reaction conditions by taking advantage of the unique redox property and carbophilic π acidity of gold. Ultimately, 3-alkynyl polysubstituted furans are synthesized concisely and regiospecifically from simple starting materials.
