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Catalytic Use of Selenium Electrophiles in Cyclizations

Danielle M. Browne, Osamu Niyomura and Thomas Wirth*

*School of Chemistry, Cardiff University, Cardiff CF10 3AT, U.K., Email: wirthcf.ac.uk

D. M. Browne, O. Niyomura, T. Wirth, Org. Lett., 2007, 9, 3169-3171.

DOI: 10.1021/ol071223y (free Supporting Information)


Abstract

A new and convenient one-pot catalytic addition-elimination reaction converted a range of (E)-3-butenoic acids into the corresponding butenolides in good yields in the presence of 5 mol % diphenyl diselenide and [bis(trifluoroacetoxy)iodo]benzene in acetonitrile.

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proposed mechanism



Key Words

Butenolides, Iodosobenzene bis(trifluoroacetate)


ID: J54-Y2007-2600