Preparation of Alkyl Di(p‑tolyl)sulfonium Salts and Their Application in Metal-Free C(sp3)–C(sp3) and C(sp3)–C(sp2) Bond Formations

Alkyldiarylsulfonium salts were synthesized by a combination of active sulfonium species, prepared through the activation of diarylsulfoxide, and alkyl nucleophiles. The isolated sulfonium salts were subjected to the allylation and cyclopropanation of the active methylene compounds and metal-free C­...

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Published inOrganic letters Vol. 25; no. 20; pp. 3766 - 3771
Main Authors Higuchi, Kazuhiro, Yamamoto, Kai, Nakamura, Shunsuke, Naruse, Haruka, Ito, Motoki, Sugiyama, Shigeo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.05.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHARGE-ACCELERATED SULFONIUM
ACID-DERIVATIVES
PYRROLOINDOLINE
ONE-POT CONSTRUCTION
INTERRUPTED PUMMERER
PHENOLS
ARYL SULFOXIDES
SULFUR
SPIROCYCLOPROPANE COMPOUNDS
C-H FUNCTIONALIZATION
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Summary:Alkyldiarylsulfonium salts were synthesized by a combination of active sulfonium species, prepared through the activation of diarylsulfoxide, and alkyl nucleophiles. The isolated sulfonium salts were subjected to the allylation and cyclopropanation of the active methylene compounds and metal-free C­(sp3)–C­(sp2) couplings via oxyallyl cation intermediates under mild conditions. The series of reactions included an umpolung strategy for the coupling of alkyl nucleophiles and metal-free C–C bond formation using sulfonium salts.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01233