A general and facile annulation of various diol motifs to [60]fullerene has been developed. This protocol can afford not only 6- to 10-membered-ring fullerenyl diethers in one step from simple acyclic diols but also directly couple [60]fullerene with a variety of structurally diverse sugars. The [60]fullerene-sugar conjugates formed do not require any linker moiety and maintain their inherent structural integrity. The electrochemistry of the fullerenyl diethers and [60]fullerene-sugar conjugates has also been investigated.
The palladium-catalyzed hydroxyl-directed C-H activation/C-O cyclization reaction of [60]fullerene with 2-phenylethyl alcohols and benzyl alcohols afforded [60]fullerene-fused tetrahydrobenzooxepine and isochroman derivatives in up to 43% yield. A plausible reaction mechanism is proposed, and the electrochemistry was also investigated.
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