Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2011 Jul 15;13(14):3746-9.
doi: 10.1021/ol2014347. Epub 2011 Jun 21.

Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes

Affiliations

Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes

Buddhadeb Chattopadhyay et al. Org Lett. .

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.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Proposed Mechanism for the Transannulation of N-tosyltriazoles with Terminal Alkynes

Similar articles

Cited by

References

    1. Chuprakov S, Hwang FW, Gevorgyan V. Angew Chem, Int Ed. 2007;46:4757. - PMC - PubMed
    1. 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.

    1. For Rh-catalyzed cycloaddition of diazocarbonyl compounds with nitriles, see: Connell R, Scavo F, Helquist P. Tetrahedron Lett. 1986;27:5559.

    1. For cyclopropanation of alkenes with 2-pyridyl diazo compounds, see: Davies HML, Townsend RJ. J Org Chem. 2001;66:6595.

    1. Horneff T, Chuprakov S, Chernyak N, Gevorgyan V, Fokin VV. J Am Chem Soc. 2008;130:14972. - PMC - PubMed

Publication types