Site-Selective Silylation of Arenes Mediated by Thianthrene S‑Oxide

The thianthrene S-oxide (TTSO)-mediated site-selective silylation of arenes has been realized via a thianthrenation/Pd-catalyzed silylation sequence. This method features a broad substrate scope and wide functional group tolerance under mild conditions and allows the synthesis of a set of (hetero)­a...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 16; pp. 6657 - 6661
Main Authors Wu, Yichen, Huang, Yu-Hao, Chen, Xiao-Yue, Wang, Peng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.08.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
PALLADIUM
ELECTROPHILIC AROMATIC-SUBSTITUTION
HETEROARENES
ACTIVATION
ARYLATION
C-H SILYLATION
SALTS
BOND SILYLATION
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Summary:The thianthrene S-oxide (TTSO)-mediated site-selective silylation of arenes has been realized via a thianthrenation/Pd-catalyzed silylation sequence. This method features a broad substrate scope and wide functional group tolerance under mild conditions and allows the synthesis of a set of (hetero)­arylsilanes with operationally simple manipulations. The application and generality of the approach were further demonstrated by the late-stage functionalization of marketed drugs. This reaction also represents the first example of a Pd-catalyzed silylation reaction of aryl sulfonium salts.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02458