Issue 32, 2015

Metal-free [3+2] cycloaddition of azides with Tf2C[double bond, length as m-dash]CH2 for the regioselective preparation of elusive 4-(trifluoromethylsulfonyl)-1,2,3-triazoles

Abstract

1,2-Dipole Tf2C[double bond, length as m-dash]CH2 is generated in situ and immediately reacts at room temperature with an azide to afford previously unknown 4-trifluoromethanesulfonyl 1,2,3-triazoles through a stepwise [3+2] cycloaddition reaction. Noteworthily, this mild and powerful uncatalyzed protocol is highly regio- and chemoselective.

Graphical abstract: Metal-free [3+2] cycloaddition of azides with Tf2C [[double bond, length as m-dash]] CH2 for the regioselective preparation of elusive 4-(trifluoromethylsulfonyl)-1,2,3-triazoles

Supplementary files

Article information

Article type
Communication
Submitted
09 Feb 2015
Accepted
17 Mar 2015
First published
17 Mar 2015

Chem. Commun., 2015,51, 6992-6995

Metal-free [3+2] cycloaddition of azides with Tf2C[double bond, length as m-dash]CH2 for the regioselective preparation of elusive 4-(trifluoromethylsulfonyl)-1,2,3-triazoles

B. Alcaide, P. Almendros and C. Lázaro-Milla, Chem. Commun., 2015, 51, 6992 DOI: 10.1039/C5CC01223F

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