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DOI: 10.1055/s-0028-1083509
FeCl2-Catalyzed Aminobromination of Alkenes Using Amides or Sulfonamides and NBS as the Nitrogen and Bromine Sources
Publication History
Publication Date:
01 October 2008 (online)
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Abstract
We have developed a convenient and efficient iron-catalyzed aminobromination of the alkenes using inexpensive FeCl2 as the catalyst, amides/sulfonamides and NBS as the nitrogen and bromine sources, respectively, under mild conditions.
Key words
iron - alkene - aminobromination - amide - sulfonamide - NBS
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
These two authors contributed equally to this work.
15
General Experimental
Procedure for Aminohalogena-tion of Alkenes
Solid
NBS (1.1 mmol, 196 mg) was added to the flask charged with FeCl2 (0.1
mmol, 13 mg), alkene (1.2 mmol), and amide or sulfonamide (1 mmol)
in EtOAc (2 mL). The solution was stirred at r.t. (25 ˚C)
or 50 ˚C for about 6 h. The resulting solution was diluted
with EtOAc (8 mL) and washed with H2O and brine. The
organic phase was dried over anhyd Na2SO4 and
concentrated under rotary evaporation, and the residue was purified
by column chromatography on silica gel (EtOAc-PE, v/v,
20:1 to 4:1) to provide the pure aminohalogenation product.
(±)-
trans
-1-(
p
-Fluorobenzamido)-2-bromocyclopentane (3b)
Yellow
oil, yield 84%. ¹H NMR (300 MHz, CDCl3): δ = 7.94-7.91
(m, 2 H), 7.09-7.04 (m, 2 H), 5.10 (t, 1 H, J = 5.9 Hz),
4.71 (t, 1 H, J = 7.2
Hz), 2.11-1.92 (m, 2 H), 1.74-1.45 (m, 4 H). ¹³C
NMR (75 MHz, CDCl3): δ = 162.9, 130.5, 124.1,
115.3, 85.1, 72.0, 34.8, 34.0, 23.3. HRMS: m/z calcd for
C12H13BrFNO [M+]:
285.0165; found: 285.0171.