Sequential One-Pot Ruthenium-Catalyzed Azide−Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide

• Published in: Journal of organic chemistry Vol. 76; no. 7; pp. 2355 - 2359
• Main Authors: Johansson, Johan R, Lincoln, Per, Nordén, Bengt, Kann, Nina
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.2011; Amer Chemical Soc
• Subjects: 3-triazoles; 4-disubstituted 1; Alkynes - chemical synthesis; Alkynes - chemistry; amines; analogs; Azides - chemical synthesis; Azides - chemistry; Catalysis; Chemistry; Chemistry, Organic; click chemistry; Cyclization; diversity; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Hydrocarbons, Halogenated - chemistry; Microwaves; Molecular Structure; organic azides; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; scope; Sodium Azide - chemistry; terminal alkynes; triazole linkages; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; ANALOGS; AMINES; SCOPE; CLICK CHEMISTRY; TERMINAL ALKYNES; DIVERSITY; TRIAZOLE LINKAGES; ORGANIC AZIDES; One pot reaction; Catalytic reaction; Acetylenic compound; Tertiary phosphine; Nitrogen heterocycle; Microwave heating; Experimental study; Organic halogen compounds; Phosphorus Organic compounds; Cycloaddition; Triazole derivatives; Microwave irradiation; Alkyne; Ruthenium complex
• ISSN: 0022-3263; 1520-6904; 1520-6904
• DOI: 10.1021/jo200134a

An experimentally simple sequential one-pot RuAAC reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields starting from an alkyl halide, sodium azide, and an alkyne, is reported. The organic azide is formed in situ by treating the primary alkyl halide with sodium azide in DMA under microwave heating. Subsequent addition of [RuClCp*(PPh3)2] and the alkyne yielded the desired cycloaddition product after further microwave irradiation.