Sequential synthesis of furans from alkynes: successive ruthenium(II)- and copper(II)-catalyzed processes.
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.
Zhang
Min
M
Laboratoire Catalyse et Organométalliques, Institut Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes, Campus de Beaulieu, 35042 Rennes, France.
Jiang
Huan-Feng
HF
Neumann
Helfried
H
Beller
Matthias
M
Dixneuf
Pierre H
PH
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*
D000480:Alkynes; D005663:Furans; D003300:Copper; D012428:Ruthenium