Hangman corroles

An article published in 2011 explored the oxygen reduction reactivity of Co hangman corroles [153], Along with novel catalytic activity, this paper described some potentially useful synthetic procedures. For example, H3tpfc was obtained in... 

Dogutan DK, Stoian SA, McGuire R Jr, Schwalbe M, Teets TS, Nocera DG (2011) Hangman corroles efficient synthesis and oxygen reaction chemistry. J Am Chem Soc 133 131-140... 

In contrast to the relatively longstanding interest in p-fluorinated porphyrins, research on the preparation and study of p-fluorinated corroles is quite new. Corroles have been shown to have distinctive coordination chemistry and lower oxidation potentials compared to porphyrins, but the coordination environment offered by corroles can chelate transition metal ions with an avidity similar to that of porphyrins. [1, 32]. Figure 3 shows the structural differences among p-octaflnorinated porphyrins, p-octafluorinated corroles, and p-octaflnorinated (with meso fluorinated aryl rings) Hangman corroles. 

In contrast to the solvent-free procedures used in the initial reports of fluorinated corrole syntheses, Chang, Ghosh, and Nocera and coworkers used the standard Lindsey approach to prepare Hangman fl-octafluorinated corrole (Fig. 3, (11)), a prosthetic group that was used to develop electrocatalysts for water splitting reactions [36]. The Nocera synthesis used a modified Lindsey approach to obtain excellent yields of (11) (29 %) after chromatographic separation of the protected xanthene protected ester, which was subsequently deprotected in 86 % yield (Scheme 13). 

Dogutan DK, McGuire R, Nocera DG (2011) Electrocatalytic water oxidation by cobalt(III) hangman p-octafluoro corroles. J Am Chem Soc 133(24) 9178-9180... 

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