Transannular [4 + 2] Cycloaddition Reactions of Cobalt-Complexed Macrocyclic Dienynes

The first transannular [4 + 2] cycloaddition reactions of macrocyclic dicobalt hexacarbonyl–dienyne complexes were demonstrated. Complexes were conveniently prepared through palladium­(II)-catalyzed intramolecular oxidative cyclization of bis­(vinylboronate esters) followed by complexation with dico...

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Bibliographic Details
Published in:Organic letters 2015-08, Vol.17 (16), p.4086-4089
Main Authors: Karabiyikoglu, Sedef, Merlic, Craig A
Format: Article
Language:English
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Summary:The first transannular [4 + 2] cycloaddition reactions of macrocyclic dicobalt hexacarbonyl–dienyne complexes were demonstrated. Complexes were conveniently prepared through palladium­(II)-catalyzed intramolecular oxidative cyclization of bis­(vinylboronate esters) followed by complexation with dicobalt octacarbonyl. Transannular [4 + 2] cycloaddition reactions of the complexes occurred at lower temperatures and shorter times than transannular Diels–Alder reactions of metal-free dienynes. Intermolecular control reactions confirmed the effect of cobalt complexation on [4 + 2] cycloaddition reactions of unactivated alkynes and dienes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01984