Organic Letters
Letter
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Scheme 6. Rh-Catalyzed Arylation to 2,3′-Biindoles
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confirmed by the single-crystal analysis of 10e.15 It was noticed
that 3j bearing a pyridinylmethyl group was recovered after it
reacted with 1,3-dimethyl-1H-indole.
In conclusion, we have developed an efficient method for the
preparation of triazoloindoles from o-alkynylanilines and
sulfonyl azides. Construction of the fragile 1-sulfonyl-1,2,3-
triazole ring was realized by stabilizing 5-copper-1,2,3-triazole
intermediate through intramolecular coordination. Although
triazoloindoles were seldom reported,16 they presented rich
chemistry in the presence of rhodium catalyst because they
could be easily transferred into the α-imino rhodium carbene
which is embedded in the indole skeleton. Through these
distinct α-imino rhodium carbenes, a variety of valuable indole
molecules were constructed, including pyrrolo[2,3-b]indoles,
spirocyclopropyl iminoindoles, 2,3-dihydropyrrolo[2,3-b]-
indoles, 3,3′-biindoles, and 2,3′-biindoles.
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V. Chem. Soc. Rev. 2010, 39, 1302.
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H.; Park, S. H.; Choi, J. H.; Chang, S. Chem.Asian J. 2011, 6, 2618.
(c) Lu, P.; Wang, Y. Synlett 2010, 2, 165.
ASSOCIATED CONTENT
* Supporting Information
Experimental procedures and characterization data for all new
compounds. This material is available free of charge via the
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S
(12) Yoo, E. J.; Ahlquist, M.; Kim, S. H.; Bae, I.; Fokin, V. V.;
Sharpless, K. B.; Chang, S. Angew. Chem., Int. Ed. 2007, 46, 1730.
(13) (a) Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org.
Lett. 2010, 12, 4952. (b) Wang, F.; Fu, H.; Jiang, Y.; Zhao, Y. Adv.
Synth. Catal. 2008, 350, 1830. (c) Cano, I.; Nicasio, M. C.; Perez, P. J.
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Y. Tetrahedron 2011, 67, 6294.
AUTHOR INFORMATION
Corresponding Authors
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Notes
The authors declare no competing financial interest.
(14) Yoo, E. J.; Chang, S. Org. Lett. 2008, 10, 1163.
ACKNOWLEDGMENTS
(15) For CIsF of 6a, 7a, and 10e, see the Supporting Information.
CCDC 968839 (6a), CCDC 968840 (7a), and CCDC 968841 (10e)
contain supplementary crystallographic data and can be obtained from
the Cambridge Crystallographic Data Centre.
(16) (a) Balli, H.; Felder, L. Helv. Chim. Acta 1978, 61, 108.
(b) Smith, P. S.; Krbechek, L. O.; Resemann, W. J. Am. Chem. Soc.
1964, 86, 2025. (c) Al-Kazwini, A. T.; O’Neill, P.; Cundall, R. B.;
Adams, G. E. Tetrahedron Lett. 1992, 33, 3045.
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We thank the financial support from the National Natural
Science Foundation of China (Nos. 21032005, 21272204, and
J1210042).
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