Visible light-promoted selective oxidation of sulfides to sulfoxides catalyzed by ruthenium porphyrins with iodobenzene diacetate

✍ Scribed by Chen, Tse-Hong; Yuan, Zhibo; Carver, Aaron; Zhang, Rui

• Book ID: 121791070
• Publisher: Elsevier Science
• Year: 2014
• Tongue: English
• Weight: 852 KB
• Volume: 478
• Category: Article
• ISSN: 0926-860X
• DOI: 10.1016/j.apcata.2014.04.014

✦ Synopsis

Under visible light irradiation, the carbonyl ruthenium(II) porphyrin complexes efficiently catalyze the selective oxidation of sulfides to sulfoxides with iodobenzene diacetate [PhI(OAc) 2 ] as the oxygen source. Various thioanisoles and allylic sulfides were oxidized to the corresponding sulfoxides without overoxidation to sulfones. The high selectivity of this unprecedented oxygen-transfer process is mechanistically rationalized by a low-reactivity ruthenium(IV)-oxo species which can be detected in the reaction of carbonyl ruthenium(II) porphyrin with iodobenzene diacetate. To the best of our knowledge, this is the first demonstration of a mild and high-yield method for the highly selective sulfoxidations by ruthenium porphyrins and PhI(OAc) 2 .