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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

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