Copper-Mediated Cascade Synthesis of Open-Cage Fullerenes

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...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-05, Vol.22 (9), p.3633-3636
Main Authors: Yamada, Michio, Ishitsuka, Asumi, Maeda, Yutaka, Suzuki, Mitsuaki, Sato, Hiroyasu
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01119