Regioselective copper(I)-catalyzed C–H hydroxylation/C–S coupling: expedient construction of 2-(styrylthio)phenols

Regioselective copper(I)-catalyzed C–H hydroxylation/C–S coupling of aryl thiols with vinyl halides was developed. Starting from substituted aryl thiols and vinyl halides, various 2-(styrylthio)phenol derivatives were efficiently prepared. The application of the synthetic methodology to generate the...

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Bibliographic Details
Published inTetrahedron Vol. 68; no. 25; pp. 5046 - 5052
Main Authors Xu, Run-Sheng, Yue, Lei, Pan, Yuan-Jiang
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.06.2012
Elsevier
Subjects
Aryl thiols
Chemistry
Chemistry, Organic
Copper-catalyzed
C–H hydroxylation/C–S coupling
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Physical Sciences
Preparations and properties
Regioselective
Science & Technology
Vinyl halides
Vinyl halides
Regioselective
Copper-catalyzed
C–H hydroxylation/C–S coupling
Aryl thiols
ACTIVATION
ARYLATION
CHIRAL SULFUR LIGANDS
SELECTIVE ALKENYLATION
PYRIDINES
BOND-CLEAVAGE
DIRECTING GROUPS
FUNCTIONALIZATION
OLEFINATION
C-H hydroxylation/C-S coupling
CHEMISTRY
Catalytic reaction
Thiol
Hydroxylation
Regioselectivity
Biological activity
Organic halogen compounds
Thiophenols
Copper ion
Styrene derivatives
Vinylic compound
Phenols
Copper I
Aromatic compound
Chemical synthesis
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Summary:Regioselective copper(I)-catalyzed C–H hydroxylation/C–S coupling of aryl thiols with vinyl halides was developed. Starting from substituted aryl thiols and vinyl halides, various 2-(styrylthio)phenol derivatives were efficiently prepared. The application of the synthetic methodology to generate the bioactive organic intermediate was also exemplified. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.04.048