Iodine catalyzed cross-dehydrogenative C-S coupling by C(sp(2))-H bond activation: direct access to aryl sulfides from aryl thiols

A novel, efficient and unprecedented green protocol for the formation of C-S bonds has been developed under metal-free conditions. This protocol involves the synthesis of aryl sulfides through the cross-dehydrogenative coupling of readily available aryl thiols with electron-rich species under solven...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 17; no. 7; pp. 4068 - 4072
Main Authors Parumala, Santosh Kumar Reddy, Peddinti, Rama Krishna
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.07.2015
Subjects
Activation
Aromatic compounds
Bonding
Chemistry
Chemistry, Multidisciplinary
Coupling
Green & Sustainable Science & Technology
Iodine
Ligands
Physical Sciences
Science & Technology
Science & Technology - Other Topics
Sulfides
Thiols
SUBSTITUTED BENZOTHIAZOLES
MILD CONDITIONS
H BOND
ATOM ECONOMY
ONE-POT SYNTHESIS
ADHESION MOLECULE-1 INTERACTION
REGIOSELECTIVE SULFENYLATION
VINYL HALIDES
DIRECT THIOLATION
HIGHLY EFFICIENT
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Summary:A novel, efficient and unprecedented green protocol for the formation of C-S bonds has been developed under metal-free conditions. This protocol involves the synthesis of aryl sulfides through the cross-dehydrogenative coupling of readily available aryl thiols with electron-rich species under solvent-free conditions and the corresponding aryl sulfides are obtained in high to quantitative yields. A catalytic amount of inexpensive and non-toxic iodine drives the reaction and no exclusion of air and expensive ligands is required.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1463-9262
1463-9270
DOI:10.1039/c5gc00403a