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Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated Ir III Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands
Author(s) -
Vaquero Mónica,
RuizRiaguas Alba,
MartínezAlonso Marta,
Jalón Félix A.,
Manzano Blanca R.,
Rodríguez Ana M.,
GarcíaHerbosa Gabriel,
Carbayo Arancha,
García Begoña,
Espino Gustavo
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801173
Subject(s) - chemistry , singlet oxygen , catalysis , chemoselectivity , aryl , alkyl , sulfur , photochemistry , oxygen atom , superoxide , medicinal chemistry , combinatorial chemistry , oxygen , organic chemistry , molecule , enzyme
A new family of heteroleptic bis‐cyclometalated Ir III complexes with formula [Ir( C N ^ ) 2 ( N N ^ )]Cl ( C N ^ =2‐phenylpyridinate andN N ^ =2,2′‐dipyridylamine or N ‐benzylated 2,2′‐dipyridylamines, were synthesized, characterized, and successfully used as photosensitizers in the catalytic photooxidation of an array of dialkyl, dibenzyl, alkyl aryl, and diaryl sulfides, as well as sulfur‐containing amino acids. Furthermore, the reactions proceeded with optimal chemoselectivity, and atom economy under mild conditions. Experimental observations support a dual mechanism in which singlet oxygen and superoxide are the actual oxidants.