Efficient synthesis of functionalized furans via ruthenium-catalyzed cyclization of epoxyalkyne derivatives.
Ruthenium catalyst TpRuPPh(3)(CH(3)CN)(2)Cl is found to effect the cyclization of epoxyalkynes to furans in the presence of Et(3)N. The reactions worked well for various epoxyalkynes with suitable oxygen and nitrogen functionalities with low loading of catalyst. It failed with disubstituted epoxyalkynes. The mechanism was elucidated by a deuterium labeling experiment that suggested that the mechanism involved a ruthenium-vinylidenium intermediate.
Lo
Ching-Yu
CY
Department of Chemistry, National Tsing-Hua University, Hsinchu, 30043 Taiwan, ROC.
Guo
Hongyun
H
Lian
Jian-Jou
JJ
Shen
Fwu-Ming
FM
Liu
Rai-Shung
RS
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry
D000480:Alkynes; D004852:Epoxy Compounds; D005663:Furans; D012428:Ruthenium