Xiaoyu Sun et al.
FULL PAPERS
erational ease; (3) mild conditions; and (4) low cata-
lytic loading. Efforts to understand the reaction mech-
anism and explore synthetic utilities of the reactions
reported here are in progress in our laboratory.
Experimental Section
General Procedure
Under nitrogen atmosphere, aziridine 1 (0.50 mmol) and
arene 2 (0.60 mmol) were added subsequently to a mixture
Scheme 3. Reaction of aziridine 1a or 5 with arene 2a or 2c.
of goldACHTRE(UGN III) chloride (1 mol%) and silver triflate (3 mol%)
in anhydrous nitromethane (2.5 mL) at room temperature.
After completion of the reaction as indicated by TLC, the
reaction mixture was quenched with water (10 mL) and ex-
tracted with EtOAc (210 mL). Evaporation of the solvent
followed by purification on silica gel afforded pure product
3. (All the products are known compounds and the data of
products was identical with the literature reports,[7] see Sup-
portingInformation.)
SupportingInformation
General experimental information, characterization data,
1
and copies of H NMR spectra of compounds 3.
Acknowledgements
We thank Professors Xue-Long Hou and Zhen Yang for
their invaluable advice during the course of this research. Fi-
nancial support from National Natural Science Foundation
of China (20502004) and the Science & Technology Commis-
sion of Shanghai Municipality (05ZR14013) is gratefully ac-
knowledged.
Scheme 4. Other reactions.
Other aziridines were also examined under the con-
ditions shown in Scheme 3. However, no product was
detected when aziridine 6 or 7 was utilized as sub-
strate and only startingmaterial was recovered, which
was similar to the previous report.[7] [Scheme 4, Eq.
(3) and Eq. (4)]. When these two reactions were per- References
formed at higher temperature (608C), the reaction
[1] For review, see: A. S. K. Hashmi, G. J. Hutchings,
turned out to be messy. However, reaction of aziri-
dine 1a with a heterocycle, such as furan 8, proceeded
smoothly under these conditions. [Scheme 4, Eq. (5)].
The reaction was finished in 2 min and the desired
product 9 was afforded in 64% yield with excellent
regioselectivity. From this case, it was found that the
efficiency of this reaction was similar to those with
electron-rich arenes.
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Conclusions
In conclusion, we have described a highly efficient
and regiospecific ring-opening reaction of aziridine
with electron-rich arene catalyzed by goldACHTER(UNG III) chlo-
ride/silver triflate, which provides a facile and conven-
ient route for the synthesis of b-arylamines. The ad-
vantages of this method include: (1) high efficiency
and excellent regioselectivity; (2) experimentally op-
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Adv. Synth. Catal. 2007, 349, 2151 – 2155