Expanding the Chemistry of Pentafluorophenyl-N-Confused Porphyrin: Diketonate Substitution and Derivatizations at the External 3-C Position of the Inverted Pyrrole Ring.

ABSTRACT: In this study, we synthesized two new 3-C-substituted pentafluorophenyl-N-confused porphyrins (PFNCPs), one with acetylacetonate (PFNCP-acac, 2a) and the other with ylidene-2-propanone (PFNCP-ac, 3a), through a one-pot reaction in the absence of a catalyst. Under mild acidic and heating conditions, the acac-substituted compound underwent acyl cleavage degradation, yielding ac-substituted product 3a. Subsequent chelation of the acac-substituted PFNCP with BF₂ resulted in a boron diketonate derivative, PFNCP-acacBF₂ (4). Additionally, an electrocyclic reaction of the ac-substituted PFNCP 3a, without a catalyst, produced a tricyclic fused [6,6,5]-TF-PFNCP (5). This tricyclic product could also be obtained directly from PFNCP-acac

SUBMITTER: Kasi B 

PROVIDER: S-EPMC11621957 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature