Paper
Trifluoromethanesulfonyloxy-group-directed regioselective (3 + 2) cycloadditions of benzynes for the synthesis of functionalized benzo-fused heterocycles.
Published Jan 14, 2015 · Takashi Ikawa, H. Kaneko, Shigeaki Masuda
Organic & biomolecular chemistry
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Abstract
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.
This study demonstrates a highly regioselective synthesis of functionalized benzo-fused heterocycles using (trifluoromethanesulfonyloxy)benzynes and 1,3-dipoles, enabling the introduction of other substituents at their ipso-
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