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  • Iron-catalyzed cross-coupling reactions of alkyl Grignards with aryl sulfamates and tosylates.

Iron-catalyzed cross-coupling reactions of alkyl Grignards with aryl sulfamates and tosylates.

Organic letters (2012-12-19)
Toolika Agrawal, Silas P Cook
ABSTRACT

The iron-catalyzed cross-coupling of aryl sulfamates and tosylates has been achieved with primary and secondary alkyl Grignards. This study of iron-catalyzed cross-coupling reactions also examines the isomerization and β-hydride elimination problems that are associated with the use of isopropyl nucleophiles. While a variety of iron sources were competent in the reaction, the use of FeF(3)•3H(2)O was critical to minimize nucleophile isomerization.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sulfamic acid, ACS reagent, 99.3%
Sigma-Aldrich
Sulfamic acid, ReagentPlus®, ≥99%
Sigma-Aldrich
Sulfamic acid, ≥99.5% (alkalimetric)
Supelco
Sulfamic acid, analytical standard (for acidimetry), ACS reagent
Sigma-Aldrich
Sulfamic acid, reagent grade, 98%
Sigma-Aldrich
Sulfamic acid, 99.999% trace metals basis
Sigma-Aldrich
Ammonium sulfamate, ACS reagent, ≥98.0%
Sigma-Aldrich
Ammonium sulfamate, BioXtra, ≥98.0%