Oxidative C-S Bond Cleavage of Benzyl Thiols Enabled by Visible-Light-Mediated Silver(II) Complexes

The oxidative cleavage reaction of the C-S bond using singlet oxygen is challenging because of its uncontrollable nature. We have developed a novel method for the singlet-oxygen-mediated selective C-S bond cleavage reaction using silver(II)-ligand complexes. Visible-light-induced silver catalysis en...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 11; pp. 4395 - 4399
Main Authors Hong, Boseok, Aganda, Kim Christopher C., Lee, Anna
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.06.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
SULFOXIDES
SINGLET MOLECULAR-OXYGEN
MECHANISM
SUPEROXIDE ION
PHOTOSENSITIZED OXIDATION
CARBONYL-COMPOUNDS
PERSULFOXIDE
ORGANIC SULFIDES
PHOTOREDOX CATALYSIS
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Summary:The oxidative cleavage reaction of the C-S bond using singlet oxygen is challenging because of its uncontrollable nature. We have developed a novel method for the singlet-oxygen-mediated selective C-S bond cleavage reaction using silver(II)-ligand complexes. Visible-light-induced silver catalysis enables the controlled oxidative cleavage of benzyl thiols to afford carbonyl compounds, such as aldehydes or ketones, which are important synthetic components.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01399