Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

One-pot synthesis of contracted and expanded porphyrins with meso-CF3 groups, from affordable precursors

Natalia Fridman, Amir Mizrahi, Zeev Gross, Irena Saltsman, magal Saphier, Qiu-cheng Chen, Matan Soll
Corrole and sapphyrin with the smallest meso-substituents reported so far were prepared in a one-pot synthesis that relies on a non-aldehydic precursor for introducing CF3 groups. The substantial amounts of products obtained by this facile pathway allowed for the full characterization of 5,10-15-tris(trifluoromethyl)corrole, the access to a variety of stable chelates thereof and investigations that disclose the unique structural and chemical properties induced by the CF3 substituents. The novel 5,10,15,20-tetra(trifluoromethyl)sapphyrin does undergo only single protonation, which according to its crystal structure is stabilized by favorable non-bonding F/H interaction between the meso-CF3 and the inverted pyrrolic NH.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201710106

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