Synthesis of 1,3,4-Trisubstituted Isoquinolines by Iodine-Mediated Electrophilic Cyclization of 2-Alkynyl Benzyl Azides


  • We thank the Japanese Society for the Promotion of Science and the Center of Excellence for financial support.


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The I's have it: A series of 2-alkynyl benzyl azides have been smoothly converted into 1,3,4-trisubstituted isoquinolines in moderate to excellent yields by an iodonium-mediated synthesis (see scheme). Depending on the structure of the substrate, iodine, Barluenga reagent (Py2IBF4/HBF4), or N-iodosuccinimide has been employed as the I+ source.