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J. J. Maresh et al.
LETTER
phenethylamines by Zn/HCl reduction at 0 °C without re-
duction of the aryl halide bond. The stability of aryl bro-
mide moieties via kinetic control at temperatures below
0 °C may extend to other zinc reduction reactions. Single-
step zinc reduction of nitrostyrenes has rarely been used in
the literature and with variable results. The reaction is sig-
nificantly lower cost, simpler than common alternative re-
duction procedures, and generates no side products.
Losses during isolation are the only limit on the yield. It is
our experience that this reaction is sensitive to the reaction
conditions, but we have described a reliable procedure
that should be widely applicable to related compounds.
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Acknowledgment
We thank the National Science Foundation CCLI A&I program
(Grant No. DUE-0310624) for support in purchasing our Bruker
Avance 300 MHz NMR spectrometer and DePaul University’s Col-
lege Sciences & Health for funding and support of this work. The
authors would also like to acknowledge the helpful assistance of
Amber Alberts, Mark D. Aparece, Emily Frank, Realino B. Gurdeal
III, and Mark Piraino for replicating the procedures described.
Supporting Information for this article is available online
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Synlett 2014, 25, 2891–2894
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