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Synfacts 2022; 18(11): 1225
DOI: 10.1055/s-0041-1738746
Polymer-Supported Synthesis

Amination and Trifluoroethylation of Fullerenes Promoted by Subphthalocyanine Capsules

Contributor(s):
Yasuhiro Uozumi
,
Shintaro Okumura
Moreno-Simoni M, Torres T, *, de la Torre G. * Universidad Autónoma de Madrid and IMDEA-Nanociencia, Madrid, Spain
Subphthalocyanine Capsules: Molecular Reactors for Photoredox Transformations of Fullerenes.

Chem. Sci. 2022;
13: 9249-9255
DOI: 10.1039/d2sc01931k.
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Key words

photoredox reaction - subphthalocyanines - amination - trifluoromethylation - fullerenes

Significance

A dimeric subphthalocyanine (SubPc) capsule (SubPc2Pd3 ) promoted the amination of C60 fullerene with aromatic (trimethylsilyl)amines in H2O/CH2Cl2 and the trifluoroethylation with CF3CH2I in CH2Cl2 under green-light irradiation to give the corresponding products in up to 86% yield (eqs. 1 and 2).


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Comment

SubPc2Pd3 was prepared according to a previously reported method (J. Am. Chem. Soc. 2013, 135, 10503). It showed a much higher activity than monomeric SubPc in both reactions, indicating that the formation of host–guest complexes between SubPc2Pd3 and the fullerene accelerates the reactions.


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Publication History

Article published online:
18 October 2022

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