KO<sup><i>t</i></sup>Bu-Mediated Coupling
of Indoles and [60]Fullerene: Transition‑Metal-Free and General
Synthesis of 1,2-(3-Indole)(hydro)[60]fullerenes
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Abstract
Direct
coupling of indoles with C<sub>60</sub> has been achieved
for the first time. Transition-metal-free KO<sup><i>t</i></sup>Bu-mediated reaction of indoles to [60]fullerene has been developed
as a practical and efficient method for the synthesis of various 1,2-(3-indole)(hydro)[60]fullerenes
that are otherwise difficult to direct synthesize in an efficient
and selective manner. This methodology tolerates sensitive functionalities
such as chloro, ester, and nitro on indole and builds molecular complexity
rapidly, with most reactions reaching completion in <1 h. A plausible
reaction mechanism is proposed to explain the high regioselectivity
at the 3-position of the indoles and the formation of 1,2-(3-indole)(hydro)[60]fullerenes