Copper-Mediated Cascade Synthesis of Open-Cage Fullerenes

Description

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An open-cage fullerene bearing an eight-membered ring orifice has been synthesized in one pot by the reaction of C60 with propargylic phosphate in the presence of CuCl. The reaction cascade involves the transformation of the phosphate to the 1,3-dienyl phosphate, which enables the reaction with C60 by [4 + 2] cycloaddition to form the cyclohexene-annulated intermediate, and subsequent intramolecular syn-elimination of the phosphodiester affords the cyclohexadiene-annulated fullerene derivative as the precursor for the open-cage fullerene.

Published: April 21, 2020

identifier:JOS-acs.orglett.0c01119

Journal

  • Organic Letters

    Organic Letters 22 (9), 3633-3636, 2020-04

    American Chemical Society

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