Ene reaction of arynes with alkynes.
Arynes, generated in situ from ortho-silylaryl triflates, undergo ene reaction with alkynes possessing propargylic hydrogen in the presence of KF/18-crown-6 in THF at room temperature to give substituted phenylallenes. Various terminal and internal alkynes as well as different arynes can be used to give the corresponding phenylallenes in good to moderate yields. The reaction of alkyne without propargylic hydrogen gave an acetylenic C-H addition product (a phenylalkyne) and a dehydro Diels-Alder product (a phenanthrene).
Department of Chemistry, Tsing Hua University, Hsinchu 30013, Taiwan.
Thiruvellore Thatai
TT
Jayanth
Masilamani
M
Jeganmohan
Mu-Jeng
MJ
Cheng
San-Yan
SY
Chu
Chien-Hong
CH
Cheng