Iodine(III)-mediated umpolung of bromide salts for the ethoxybromination of enamides.

Iodine(III)-mediated umpolung of bromide salts for the ethoxybromination of enamides.

Organic letters (2013-04-02)

Sophie Nocquet-Thibault, Pascal Retailleau, Kevin Cariou, Robert H Dodd

ABSTRACT

Using (diacetoxyiodo)benzene in conjunction with simple bromide salts in ethanol allows the regioselective ethoxybromination of a wide range of enamides, thus yielding highly versatile α-bromo hemiaminals, which can then be engaged in a broad array of transformations.

MATERIALS

Product Number

Brand

Product Description

411515

Sigma-Aldrich

Lithium bromide solution, 54 wt. % in H₂O

213225

Sigma-Aldrich

Lithium bromide, ReagentPlus^®, ≥99%

429465

Sigma-Aldrich

Lithium bromide, AnhydroBeads^™, −10 mesh, 99.999% trace metals basis

449873

Sigma-Aldrich

Lithium bromide, AnhydroBeads^™, −10 mesh, ≥99.9% trace metals basis

229733

Sigma-Aldrich

Lithium bromide, powder and chunks, ≥99.995% trace metals basis