Anion−π
Catalysis on Fullerenes
Version 2 2018-06-22, 23:43
Version 1 2017-09-13, 18:56
Posted on 2018-06-22 - 23:43
Anion−π
interactions on fullerenes are about as poorly
explored as the use of fullerenes in catalysis. However, strong exchange-correlation
contributions and the localized π holes on their surface promise
unique selectivities. To elaborate on this promise, tertiary amines
are attached nearby. Dependent on their positioning, the resulting
stabilization of anionic transition states on fullerenes is shown
to accelerate disfavored enolate addition and exo Diels–Alder reactions enantioselectively. The found
selectivities are consistent with computational simulations, particularly
concerning the discrimination of differently planarized and charge-delocalized
enolate tautomers by anion−π interactions. Enolate−π
interactions on fullerenes are much shorter than standard π–π
interactions and anion−π interactions on planar surfaces,
and alternative cation−π interactions are not observed.
These findings open new perspectives with regard to anion−π
interactions in general and the use of carbon allotropes in catalysis.
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López-Andarias, Javier; Frontera, Antonio; Matile, Stefan (2017). Anion−π
Catalysis on Fullerenes. ACS Publications. Collection. https://doi.org/10.1021/jacs.7b08113
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AUTHORS (3)
JL
Javier López-Andarias
AF
Antonio Frontera
SM
Stefan Matile