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A Conjunctive Carboiodination: Indenes by a Double Carbopalladation–Reductive Elimination Domino Process

Authors

  • Dr. Xiaodong Jia,

    1. Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
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  • David A. Petrone,

    1. Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
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  • Prof. Dr. Mark Lautens

    Corresponding author
    1. Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
    • Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada)
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  • This research was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), the Merck Frosst Centre for Therapeutic Research, and the University of Toronto. X.J. thanks Northwest Normal University (China) for research support at the University of Toronto. We thank Dr. Alan Lough (University of Toronto) for the X-ray structure of 5. We thank Johnson Matthey for the donation of palladium catalysts.

Abstract

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Something gained, nothing lost: A Pd0-catalyzed domino intermolecular/intramolecular process terminated by carbohalogenation is reported. In this reaction, two new C[BOND]C bonds, one new C[BOND]I bond and one five-membered ring are formed in a single step, and all of the atoms in the starting materials are incorporated into the product (see scheme).

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