Intermolecular Hydroalkoxylation of Terminal Alkynes Catalyzed by a Dipyrrinato Rhodium(I) Complex with Unusual Selectivity

Raphael H. Lam, D. Barney Walker, Matthew H. Tucker, Mark R D Gatus, Mohan Bhadbhade, Barbara A. Messerle*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    16 Citations (Scopus)

    Abstract

    An operationally simple and atom-economical method for the E-selective preparation of enol ethers is described. A novel dicarbonyl(5-phenyldipyrrinato)rhodium complex, 2, was prepared in four synthetic steps, characterized by X-ray crystallography and NMR spectroscopy, and then investigated as a catalyst for the intermolecular hydroalkoxylation of terminal alkynes. Solvent and substrate studies were used to gain insight into the mechanism of the reaction. Cyclic voltammetry was also used to investigate the electronic properties of 2. The rhodium(I)-catalyzed intermolecular alkyne hydroalkoxylation reaction reported here mediates excellent substrate transformation with a high degree of E/Z selectivity which is opposite to that reported previously using alternative catalysts.

    Original languageEnglish
    Pages (from-to)4312-4317
    Number of pages6
    JournalOrganometallics
    Volume34
    Issue number17
    DOIs
    Publication statusPublished - 14 Sep 2015

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