Synthesis of Bicyclic Enediynes from Bis[phenyl[(trifluoromethanesulfonyl)oxy]iodo]acetylene:  A Tandem Diels−Alder/Palladium(II)- and Copper(I)-Cocatalyzed Cross-Coupling Approach

The reaction of bicycloalkenylbis(phenyliodonium) triflates 1a or b (available via the Diels−Alder reaction of bis[phenyl[(trifluoromethanesulfonyl)oxy]iodo]acetylene with cyclopentadiene or furan, respectively) with alkynylstannanes 2a − g at room temperature in DMF in the presence of catalytic amo...

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Bibliographic Details
Published in:Journal of organic chemistry 1996-09, Vol.61 (18), p.6162-6165
Main Authors: Ryan, John H, Stang, Peter J
Format: Article
Language:English
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Summary:The reaction of bicycloalkenylbis(phenyliodonium) triflates 1a or b (available via the Diels−Alder reaction of bis[phenyl[(trifluoromethanesulfonyl)oxy]iodo]acetylene with cyclopentadiene or furan, respectively) with alkynylstannanes 2a − g at room temperature in DMF in the presence of catalytic amounts of trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) and copper(I) iodide proceeds smoothly and with selectivity to afford good to excellent yields of bicyclic enediynes 3a − k.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo960750k