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  • One-pot anti-Markovnikov hydroamination of unactivated alkenes by hydrozirconation and amination.

One-pot anti-Markovnikov hydroamination of unactivated alkenes by hydrozirconation and amination.

The Journal of organic chemistry (2013-08-01)
Alexandra E Strom, John F Hartwig
ABSTRACT

A one-pot anti-Markovnikov hydroamination of alkenes is reported. The synthesis of primary and secondary amines from unactivated olefins was accomplished in the presence of a variety of functional groups. Hydrozirconation, followed by amination with nitrogen electrophiles, provides exclusive anti-Markovnikov selectivity. Most products are isolated in high yields without the use of column chromatography.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Zirconium, powder, −100 mesh
Sigma-Aldrich
Zirconium, sponge, ≥99% trace metals basis
Sigma-Aldrich
Zirconium, rod, diam. 6.35 mm, ≥99% trace metals basis
Sigma-Aldrich
Zirconium, foil, thickness 0.1 mm, 99.98% trace metals basis