Facile Synthesis of Multisubstituted Benzo[b]furans via 2,3-Disubstituted 6,7-Furanobenzynes Generated from ortho-Iodoaryl Triflate-type Precursors

2,3-Disubstituted 6,7-furanobenzynes were efficiently generated from ortho-iodoaryl triflate-type precursors using a silylmethyl Grignard reagent as the activator. The reactions between 6,7-furanobenzynes and unsymmetrical arynophiles proceeded in a highly regioselective manner. Since a variety of p...

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Bibliographic Details
Published in:Chemistry letters 2017-01, Vol.46 (1), p.118-121
Main Authors: Morita, Takamoto, Nishiyama, Yoshitake, Yoshida, Suguru, Hosoya, Takamitsu
Format: Article
Language:English
Subjects:
Furans
Precursors
Reagents
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Summary:2,3-Disubstituted 6,7-furanobenzynes were efficiently generated from ortho-iodoaryl triflate-type precursors using a silylmethyl Grignard reagent as the activator. The reactions between 6,7-furanobenzynes and unsymmetrical arynophiles proceeded in a highly regioselective manner. Since a variety of precursors were easily synthesizable from readily available 2,3-disubstituted 6-hydroxybenzofurans, this method enabled facile synthesis of a wide range of multisubstituted benzofurans, including π-extended molecules.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.160951