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RSC Advances
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ARTICLE
Journal Name
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Scheme 2. Proposed mechanism.
As an example of the synthetic utilities of (E)-bromoalkenes, 2a
was converted into the corresponding (E)-phenylselenostyrene 4 by
a previously reported procedure.34 The compound 2a (0.5 mmol)
was reacted with the nucleophilic selenium species, generated in
situ by reacting diphenyl diselenide 3 (0.3 mmol) and NaBH4 in PEG-
400 at room temperature. After
4 h at 120 °C, (E)-
7.
phenylselenostyrene was isolated in 72% yield with total
4
retention of the stereochemistry of the double bond (Scheme 3).
Furthermore some of us reported that 2a can react with PhSeZnCl
in ‘on water’ conditions affording 4 in 2 h and 94% yield.35
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.
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Conclusions
In summary, we have developed a simple and efficient method to
hydrodebromination of 1,1-dibromoalkenes in the presence of 10
mol% of tellurium and NaBH4 in ethanol. This transition metal-free
protocol is suitable to several 1,1-dibromoalkenes, affording the
corresponding (E)-bromoalkenes in good yields and excellent
stereoselectivity in short reaction times and under mild reaction
conditions.
Acknowledgements
The authors thank FAPERGS, CNPq and CAPES for financial support.
CNPq is also acknowledged for the fellowship for G.P. and E.J.L. This
work is part of the scientific collaborations carried out under the
umbrella of the Network SeS-Redox and Catalysis.
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Notes and references
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2.
G. Chelucci, Chem. Rev., 2012, 112, 1344.
F. Ramirez, N. B. Desal and N. McKelvie, J. Am. Chem. Soc.,
1962, 84, 1745.
4 | J. Name., 2012, 00, 1-3
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