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

Paper ID Volume ID Publish Year Pages File Format Full-Text
39698 45831 2014 8 PDF Available
Title
Visible light-promoted selective oxidation of sulfides to sulfoxides catalyzed by ruthenium porphyrins with iodobenzene diacetate
Abstract

•We report a new highly selective catalytic sulfoxidations using ruthenium porphyrins and iodobenzene diacetate.•We examine the reaction conditions and explore the substrate scope.•We propose a mechanism in light of detecting the key oxidizing intermediate.

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.

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Keywords
Por, porphyrin dianion; TMP, 5,10,15,20-tetramesitylporphyrin dianion; TPFPP, 5,10,15,20-tetrakispentafluorophenylporphyrin dianion; PhI(OAc)2, iodobenzene diacetate; PhIO, iodosobenzene; TBHP, tert-butyl hydroperoxide; m-CPBA, m-chloroperoxybenzoic acid;
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Visible light-promoted selective oxidation of sulfides to sulfoxides catalyzed by ruthenium porphyrins with iodobenzene diacetate
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 478, 20 May 2014, Pages 275–282
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us