Synthesis of Fused Dihydroazepine Derivatives of Fullerenes by a Rh‐Catalyzed Cascade Process

A synthetic methodology is reported that functionalizes C60 and C70 fullerenes with dihydroazepine rings by a cascade reaction encompassing a rhodium‐catalyzed cycloisomerization of 1,5‐bisallenes and a [4+2] cycloaddition. This transition metal‐catalyzed cascade reaction provides a versatile and st...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-08, Vol.363 (15), p.3835-3844
Main Authors: Artigas, Albert, Castanyer, Cristina, Roig, Nil, Lledó, Agustí, Solà, Miquel, Pla‐Quintana, Anna, Roglans, Anna
Format: Article
Language:English
Subjects:
Adducts
Cascade chemical reactions
Cycloaddition
Density Functional Calculations
Electrochemical analysis
Fullerenes
Isomerization
Perovskites
Photovoltaic cells
Rhodium
Solar Cells
Transition metals
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Summary:A synthetic methodology is reported that functionalizes C60 and C70 fullerenes with dihydroazepine rings by a cascade reaction encompassing a rhodium‐catalyzed cycloisomerization of 1,5‐bisallenes and a [4+2] cycloaddition. This transition metal‐catalyzed cascade reaction provides a versatile and step‐economical approach to the synthesis of 6,7‐membered polyheterocyclic fullerene adducts. Electrochemical characterization of the products obtained ventures their application in organic and perovskite photovoltaic devices.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100644