Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes
- PMID: 21692488
- PMCID: PMC3156790
- DOI: 10.1021/ol2014347
Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes
Abstract
The first transannulation of 1,2,3-triazoles with terminal alkynes into pyrroles is reported. The reaction proceeds in the presence of a Rh(2)(oct)(4)/AgOCOCF(3) binary catalyst system providing a straightforward approach to 1,2,4-trisubstituted pyrroles in good to excellent yields.
© 2011 American Chemical Society
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For representative examples on the Rh-catalyzed reactions of diazocarbonyl compounds with alkynes, see: Davies HML, Romines KR. Tetrahedron. 1988;44:3343.Kinder FR, Padwa A. Tetrahedron Lett. 1990;31:6835.Padwa A, Kassir JM, Xu SL. J Org Chem. 1991;56:6971.Davies HML, Cantrell WR, Romines KR, Jr, Baum JS. Org Synth. 1992;70:93.Doyle MP, Winchester WP, Hoorn JAA, Lynch V, Simonsen SH, Ghosh R. J Am Chem Soc. 1993;115:9968.Padwa A, Kinder FR. J Org Chem. 1993;58:21.Doyle MP, Protopopova M, Müller P, Ene D, Shapiro EA. J Am Chem Soc. 1994;116:8492.
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For Rh-catalyzed cycloaddition of diazocarbonyl compounds with nitriles, see: Connell R, Scavo F, Helquist P. Tetrahedron Lett. 1986;27:5559.
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For cyclopropanation of alkenes with 2-pyridyl diazo compounds, see: Davies HML, Townsend RJ. J Org Chem. 2001;66:6595.
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