Trifluoromethanesulfonyloxy-group-directed regioselective (3 + 2) cycloadditions of benzynes for the synthesis of functionalized benzo-fused heterocycles.
Highly regioselective (3 + 2) cycloadditions of (trifluoromethanesulfonyloxy)benzynes [(triflyloxy)benzynes] with 1,3-dipoles followed by cross-coupling reactions provided multisubstituted benzo-fused heterocycles. The triflyloxy group at the 3-position of benzynes, and even that at the remote 4-position, greatly affected the regiocontrol of the cycloaddition. These groups also served to install other substituents at their ipso-positions.
Graduate School of Pharmaceutical Sciences, Osaka University, Yamadaoka, Suita, Osaka 565-0871, Japan. ikawa@phs.osaka-u.ac.jp akai@phs.osaka-u.ac.jp.
Takashi
T
Ikawa
Hideki
H
Kaneko
Shigeaki
S
Masuda
Erika
E
Ishitsubo
Hiroaki
H
Tokiwa
Shuji
S
Akai
D001555:Benzene Derivatives / Q000737:chemistry*; D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D001555:Benzene Derivatives; D006571:Heterocyclic Compounds; C524146:benzyne