One-Pot Synthesis of Contracted and Expanded Porphyrins with meso-CF3 Groups

Qiu-Cheng Chen; Matan Soll; Amir Mizrahi; Irena Saltsman; Natalia Fridman; Magal Saphier; Zeev Gross

doi:10.1002/anie.201710106

One-Pot Synthesis of Contracted and Expanded Porphyrins with meso-CF₃ Groups

Angew Chem Int Ed Engl. 2018 Jan 22;57(4):1006-1010. doi: 10.1002/anie.201710106. Epub 2017 Dec 29.

Authors

Qiu-Cheng Chen¹, Matan Soll¹, Amir Mizrahi^{1

2}, Irena Saltsman¹, Natalia Fridman¹, Magal Saphier², Zeev Gross¹

Affiliations

¹ Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, 32000, Israel.
² Chemistry Department, Nuclear Research Centre Negev, P.O.B. 9001, Beer Sheva, 84190, Israel.

PMID: 29134761
DOI: 10.1002/anie.201710106

Abstract

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 undergoes 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.

Keywords: 2-bromo-2-chloro-1,1,1-trifluoroethane; corrole; porphyrin; sapphyrin; trifluoromethyl.

Publication types

Research Support, Non-U.S. Gov't