Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides.
[reaction: see text] We have successfully prepared potassium azidoalkyltrifluoroborates from the corresponding halogen compounds in 94-98% yields through a nucleophilic substitution reaction with NaN(3). In the presence of various alkynes and Cu(I) as a catalyst, these azidotrifluoroborates easily formed 1,4-disubstituted organo-[1,2,3]-triazol-1-yl-trifluoroborates in 85-98% yields. This method was then developed into a facile one-pot synthesis for the preparation of various organo-[1,2,3]-triazol-1-yl-trifluoroborates using haloalkyltrifluoroborates as the starting materials.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, 19104-6323, USA. gmolandr@sas.upenn.edu
Ham
Jungyeob
J
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D001881:Borates / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
D000480:Alkynes; D001386:Azides; D001881:Borates; D006845:Hydrocarbons, Fluorinated; D003300:Copper