Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 2, Pages 531-535Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405729
Keywords
cycloadditions; density functional calculations; homogeneous catalysis; iridium; seven-membered rings
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Funding
- Swedish Research Council
- Royal Physiographical Society
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Third-row transition metal catalysts remain a largely untapped resource in cycloaddition reactions for the formation of medium-sized rings. Herein, we report the first examples of iridium-catalyzed inter-and intramolecular vinylcyclopropane (VCP)-alkyne (5+2) cycloadditions. DFT modeling suggests that catalysis by iridium(I) proceeds through a mechanism similar to that previously reported for rhodium(I)-catalyzed VCP-alkyne cycloadditions, but a smaller free energy span for iridium enables substantially faster catalysis under favorable conditions. The system is characterized by up to quantitative yields and is amenable to an array of disubstituted alkynes and vinylcyclopropanes.
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