Efficient synthesis of 2-substituted-1,2,3-triazoles.
In this three-component reaction, alkynes undergo a copper(I)-catalyzed cycloaddition with sodium azide and formaldehyde to yield 2-hydroxymethyl-2 H-1,2,3-triazoles, which are useful intermediates that can be readily converted to polyfunctional molecules. The hydroxymethyl group can also be removed, providing convenient access to N H-1,2,3-triazoles. The reaction is experimentally simple and readily scalable.
Kalisiak
Jarosław
J
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Sharpless
K Barry
KB
Fokin
Valery V
VV
D000480:Alkynes / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D005557:Formaldehyde / Q000737:chemistry; D019810:Sodium Azide / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis*
D000480:Alkynes; D014230:Triazoles; D005557:Formaldehyde; D019810:Sodium Azide