Organic Letters
Letter
the distribution of deuterium on 1a and 3a was evaluated. In
these reaction conditions, 29% of 3a was formed with a D/H
ratio of 35:65 at the C3 position of 3a, and 59% of 1a was
recovered with a D/H ratio of 56:44 at the C3 position (Scheme
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4a). These results suggest that indolium is readily formed, and
Starikova, Z. A. Eur. J. Org. Chem. 2000, 2000, 3323. (b) Zhun, I. V.;
Ignatenko, A. V. Russ. Chem. Bull. 2004, 53, 2221.
H/D exchange reaches equilibrium before the nucleophilic
addition of 2a (Scheme 4b). Therefore, we conclude that the
nucleophilic addition by 2 was the rate-determining step.
In conclusion, we have exploited the formation of indolium
from N-acetylindole using BF ·OEt in (CF ) CHOH to allow
(
11) (a) Nowrouzi, F.; Batey, R. A. Angew. Chem., Int. Ed. 2013, 52,
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́
(12) (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
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3
2
3 2
C2 site-selective intermolecular nucleophilic addition of an
electron-rich aromatic compound. We believe that this approach
opens a new synthetic strategy to produce more diverse indoline
derivatives.
(13) (a) Mustafin, A. G.; Dyachenko, D. I.; Gataullin, R. R.;
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(
́ ́
14) (a) Begue, J. P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18.
ASSOCIATED CONTENT
Supporting Information
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(b) Eberson, L.; Hartshorn, M. P.; Persson, O.; Radner, F. Chem.
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S
Experimental procedures and characterization of the
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AUTHOR INFORMATION
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*
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d) Kametani, T.; Ogasawara, K. J. Chem. Soc. C 1967, 0, 2208.
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Notes
The authors declare no competing financial interest.
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