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

doi:10.1021/acs.joc.8b02886

Paper

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

Published Jan 14, 2019 · Elwira Bisz, M. Szostak

The Journal of organic chemistry

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13

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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.

Study Snapshot

Iron-catalyzed C(sp2)-C(sp3) cross-coupling of chlorobenzosulfonamides with alkyl Grignard reagents provides high to excellent yields of alkylated benzosulfonamides for medicinal chemistry applications and trace

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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