6533b836fe1ef96bd12a0b1d
RESEARCH PRODUCT
Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Chlorobenzenesulfonamides with Alkyl Grignard Reagents: Entry to Alkylated Aromatics
Elwira BiszMichal SzostakMichal Szostaksubject
chemistry.chemical_classification010405 organic chemistryIron catalyzedOrganic ChemistryPlasticizerAlkylation010402 general chemistry01 natural sciences0104 chemical scienceschemistry.chemical_compoundchemistryReagentOrganic chemistryOrganic synthesisAlkyldescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-12-21 | Journal of Organic Chemistry |