A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes.
[3 + 2]-Cycloadditions of alkyl azides with various unsymmetrical internal alkynes in the presence of CpRuCl(PPh3)2 as catalyst in refluxing benzene have been examined, leading to 1,4,5-trisubstituted-1,2,3-triazoles. Whereas alkyl phenyl and dialkyl acetylenes undergo cycloadditions to afford mixtures of regioisomeric 1,2,3-triazoles, acyl-substituted internal alkynes react with complete regioselectivity. In addition, propargyl alcohols and propargyl amines were found to react with azides to afford single regioisomeric products.
Majireck
Max M
MM
Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Weinreb
Steven M
SM
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001386:Azides; D012428:Ruthenium