6533b7cffe1ef96bd1257cb0

RESEARCH PRODUCT

Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates

Elwira Bisz

subject

Pharmaceutical ScienceAlkylationArticleCoupling reactionAnalytical ChemistryCatalysischemistry.chemical_compoundironQD241-441Drug Discoverycross-couplingOrganic chemistryPhysical and Theoretical ChemistryAlkylchemistry.chemical_classificationChemistryArylOrganic ChemistrySulfonateChemistry (miscellaneous)Fe-catalysisReagentUreaKumada cross-couplingMolecular MedicineC–O activationaryl sulfonates

description

Aryl sulfonate esters are versatile synthetic intermediates in organic chemistry as well as attractive architectures due to their bioactive properties. Herein, we report the synthesis of alkyl-substituted benzenesulfonate esters by iron-catalyzed C(sp2)–C(sp3) cross-coupling of Grignard reagents with aryl chlorides. The method operates using an environmentally benign and sustainable iron catalytic system, employing benign urea ligands. A broad range of chlorobenzenesulfonates as well as challenging alkyl organometallics containing β-hydrogens are compatible with these conditions, affording alkylated products in high to excellent yields. The study reveals that aryl sulfonate esters are the most reactive activating groups for iron-catalyzed alkylative C(sp2)–C(sp3) cross-coupling of aryl chlorides with Grignard reagents.

yearjournalcountryeditionlanguage
2021-09-29Molecules
https://doi.org/10.3390/molecules26195895