A novel hypervalent iodine reagent prepared from o-iodosylbenzoic acid and trifluoromethanesulfonic acid preparation and reactions of alkynyl( o-carboxyphenyl)iodonium triflates

A hyervalent iodine reagent prepared from o-iodosylbenzoic acid and trifluoromethanesulfonic acid (TfOH) (1:2) showed a high reactivity toward aromatic substrates, giving aryl( o-carboxyphenyl)iodonium triflates in good to high yields. Treatment of the iodine reagent with 1-trimethylsilylalkynes aff...

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Bibliographic Details
Published in:Tetrahedron letters 1995-02, Vol.36 (7), p.1081-1084
Main Authors: Kitamura, Tsugio, Nagata, Kensuke, Taniguchi, Hiroshi
Format: Article
Language:English
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Summary:A hyervalent iodine reagent prepared from o-iodosylbenzoic acid and trifluoromethanesulfonic acid (TfOH) (1:2) showed a high reactivity toward aromatic substrates, giving aryl( o-carboxyphenyl)iodonium triflates in good to high yields. Treatment of the iodine reagent with 1-trimethylsilylalkynes afforded alkynyliodonium triflates bearing carboxy group in high yields. The alkynyliodonium triflates indicated a high efficiency as a Michael acceptor to nucleophiles and the o-carboxyphenyliodonio group behaved as a good leaving group. Alkynyliodonium triflates 3 were prepared and reacted with nucleophiles.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(94)02459-O