Straightforward Synthesis of a Fluorous Tetraarylporphyrin: an Efficient and Recyclable Sensitizer for Photooxygenation Reactions

Abstract

AbstractA fluorous tetraarylporphyrin has been prepared in a single reaction step starting from commercially available 5,10,15,20‐tetrakis(4‐hydroxyphenyl)porphyrin [TPP(OH)4]. The new compound was successfully employed as a sensitizer in photooxygenation reactions carried out under homogeneous conditions, showing activity comparable to the standard 5,10,15,20‐tetraphenylporphyrin (TPP) sensitizer. Photooxygenation reactions were also investigated under fluorous biphasic conditions, yielding somewhat different product distributions. Because of its fluorous nature, the new porphyrin could be easily removed from the homogeneous mixture by liquid‐liquid or solid phase extraction. In the case of fluorous biphasic reactions, the fluorous sensitizer could be recovered by simple phase separation and then reused, maintaining its efficiency at least upon five subsequent runs.