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Iridium Catalyzed Carbocyclizations: Efficient (5+2) Cycloadditions of Vinylcyclopropanes and Alkynes.

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Author

Summary, in English

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.

Publishing year

2015

Language

English

Pages

531-535

Publication/Series

Chemistry: A European Journal

Volume

21

Issue

2

Document type

Journal article

Publisher

Wiley-Blackwell

Topic

  • Chemical Sciences

Status

Published

ISBN/ISSN/Other

  • ISSN: 1521-3765