Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited.
After revisiting earlier works reporting the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via the addition of bromomagnesium acetylides to azides, much improved yields of the products were obtained for a wide array of azides and alkynes. The intermediates of that reaction can be trapped with different electrophiles to regioselectively form 1,4,5-trisubstituted 1,2,3-triazoles. [reaction: see text]
Krasiński
Antoni
A
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA. kranik@scripps.edu
Fokin
Valery V
VV
Sharpless
K Barry
KB
D000114:Acetylene / Q000031:analogs & derivatives; D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis*
D000480:Alkynes; D001386:Azides; D001965:Bromides; D014230:Triazoles; D008274:Magnesium; D000114:Acetylene