Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 7, Pages 1548-1568Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403503
Keywords
Porphyrinoids; Nucleophilic substitution; Fluorine; Lipophilicity; Alcohols
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Funding
- Deutsche Forschungsgemeinschaft (DFG) (Graduate School 1582 - Fluorine as a Key Element, Freie Universitat Berlin)
- Bundesministeriums fur Bildung und Forschung (BMBF) [FKZ: 13N11032]
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A detailed study of the nucleophilic aromatic substitution reaction of meso-pentafluorophenyl-substituted tetrapyrrole systems with different alcohols is presented. The systematic investigation of various alcohols and bases in two different solvents led to optimized reaction conditions, allowing the selective substitution of the p-fluorine atoms of meso-pentafluorophenyl-substituted porphyrins, their zinc complexes, and a meso-tris(pentafluorophenyl) corrole with alcohols and a simple base in high yields. When applied to A(3)B porphyrins in combination with suitable protecting groups, functionalized, polar A(3)B porphyrins can be prepared in a simple two-step one-pot procedure. By using the nucleophilic aromatic substitution reaction, a dimeric porphyrin system was synthesized. In addition, the copper(I)-catalyzed 1,3-dipolar cycloaddition of properly functionalized meso-pentafluorophenyl-substituted porphyrins led to the corresponding porphyrin dimer with a 1,2,3-triazole linker. The method described herein allows a simple and fast approach towards multifunctionalized porphyrinoids based on meso-pentafluorophenyl- substituted tetrapyrroles.
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