Au/Ag-catalyzed intramolecular ring-opening of vinylidene-cyclopropanes (VDCPs): an easy access to functional tetrahydropyrans.
An intramolecular ring-opening of vinylidenecyclopropanes (VDCPs) tethered with alcohol chains has been established. A series of transition metal catalysts and their combinations have been screened under mild conditions, and a cocatalyst system consisting of [(Ph(3)PAu)(3)O]BF(4) (4 mol %) and AgOTf (4 mol %) was found to catalyze the reaction to completion within 10-30 min in 1,4-dioxane at 60 degrees C to give allene-functionalized tetrahydropyrans.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China.
Wei
W
Li
Wei
W
Yuan
Surech
S
Pindi
Min
M
Shi
Guigen
G
Li
D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013696:Temperature
D003521:Cyclopropanes; D011714:Pyrans; D012834:Silver; D006046:Gold