Zhang Min, Jiang Huan-Feng, Neumann Helfried, Beller Matthias, Dixneuf Pierre H
Laboratoire Catalyse et Organométalliques, Institut Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes, Campus de Beaulieu, 35042 Rennes, France.
Angew Chem Int Ed Engl. 2009;48(9):1681-4. doi: 10.1002/anie.200805531.
Step in time: 2,5-Disubstituted furans can be prepared from terminal alkynes in one pot using two successive catalytic reactions (see scheme; p-TSA = para-toluenesulfonic acid). First, a 1,3-dienyl alkyl ether is produced by the dimerization of a terminal alkyne and addition of an alcohol catalyzed by [RuCp*(NCMe)(3)][PF(6)]. Then, consecutive hydrolysis and cyclization catalyzed by CuCl(2) provides the 2,5-disubstituted furan.
2,5-二取代呋喃可以通过两个连续的催化反应,由端炔一锅法制备(见方案;对甲苯磺酸 = 对甲苯磺酸)。首先,在[RuCp*(NCMe)(3)][PF(6)]催化下,端炔二聚并加入醇生成1,3-二烯基烷基醚。然后,由CuCl(2)催化的连续水解和环化反应生成2,5-二取代呋喃。