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. 2013 Mar 27;135(12):4652-5.
doi: 10.1021/ja400350c. Epub 2013 Mar 15.

Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes

Stepan Chuprakov  1 , Sen Wai Kwok, Valery V Fokin
Affiliations

Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes

Stepan Chuprakov et al. J Am Chem Soc. .

Abstract

Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazole-diazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle.

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Figures

Figure 1
Figure 1
Rhodium(II) carboxylates used in this study.
Scheme 1
Scheme 1
Desulfonylation of Mesyl-Protected Transannulation Products.
See this image and copyright information in PMC

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References

    1. For cyclopropanation, see: Chuprakov S, Kwok SW, Zhang L, Lercher L, Fokin VV. J. Am. Chem. Soc. 2009;131:18034. Grimster N, Zhang L, Fokin VV. J. Am. Chem. Soc. 2010;132:2510. Zibinsky M, Fokin VV. Org. Lett. 2011;13:4870. Chuprakov S, Gevorgyan V. Org. Lett. 2007;9:4463. Alford JS, Davies HML. Org. Lett. 2012;14:6020. For carbenoid insertions, see: Chuprakov S, Malik JA, Zibinsky M, Fokin VV. J. Am. Chem. Soc. 2011;133:10352. Miura T, Biyajima T, Fujii T, Murakami M. J. Am. Chem. Soc. 2012;134:194. For 1,2-alkyl shift, see: Selander N, Worrell BT, Fokin VV. Angew. Chem. Int. Ed. 2012;51:13054. Miura T, Funakoshi Y, Morimoto M, Biyajima T, Murakami M. J. Am. Chem. Soc. 2012;134:17440. Gulevich AV, Gevorgyan V. Angew. Chem. Int. Ed. 2013;52:1371. For arylation with boronic acids, see: Selander N, Worrell BT, Chuprakov S, Velaparthi S, Fokin VV. J. Am. Chem. Soc. 2012;134:14670.

    1. For review, see: Chattopadhyay B, Gevorgyan V. Angew. Chem. Int. Ed. 2012;51:862.

    1. Horneff T, Chuprakov S, Chernyak N, Gevorgyan V, Fokin VV. J. Am. Chem. Soc. 2008;130:14972. Zibinsky M, Fokin VV. Angew. Chem., Int. Ed. 2013;52:1507. For N-fused imidazoles, see: Chuprakov S, Hwang FW, Gevorgyan V. Angew. Chem., Int. Ed. 2007;46:4757.

    1. Miura T, Yamauchi M, Murakami M. Chem. Commun. 2009:1470. - PubMed
    2. Chattopadhyay B, Gevorgyan V. Org. Lett. 2011;13:3746. - PMC - PubMed

    1. For isolated reports, see: Hubert AJ, Feron A, Warin R, Teyssie P. Tetrahedron Lett. 1976:1317. Drapier J, Feron A, Warin R, Hubert AJ, Teyssie P. Tetrahedron Lett. 1979:559. Bien S, Kimmel T, Tirosh N. Acta Chem. Scand. 1993;47:218.

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