Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Chlorobenzenesulfonamides with Alkyl Grignard Reagents: Entry to Alkylated Aromatics

Elwira Bisz, Michal Szostak

Research output: Contribution to journalArticle

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Abstract

Alkylated benzosulfonamides are compounds of high importance in organic synthesis, including the production of pharmaceuticals, agrochemicals, and plasticizers. We report the iron-catalyzed C(sp2)-C(sp3) cross-coupling of chlorobenzosulfonamides with alkyl Grignard reagents under mild and sustainable conditions. Electronically and sterically varied benzosulfonamides as well as challenging alkyl organometallics containing β-hydrogen afford alkylated benzosulfonamides in high to excellent yields. Sulfonamide represents the most reactive activating group for iron-catalyzed cross-coupling. The process affords alkylated benzenesulfonamides poised for medicinal chemistry applications and traceless reductive cleavage. ©

Original languageEnglish (US)
Pages (from-to)1640-1646
Number of pages7
JournalJournal of Organic Chemistry
Volume84
Issue number3
DOIs
StatePublished - Feb 1 2019

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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