An efficient approach to azidation of aryl halides is described here. Good yields of aryl azides were obtained with [CuI/EDTA]–3 as a catalytic system. Cost-affectivity of the EDTA compared to expensive DMEDA (1 : 500 times) along with the use of 7EtOH:3H2O as mixed solvent and green medium makes it to be a suitable method for selective synthesis of aryl azides.
BräseS., GilC., KnepperK. and ZimmermannV., Organic azides: an exploding diversity of a unique class of compounds, Angewandte Chemie International Edition44(33) (2005), 5188–5240.
2.
MaejimaT., UedaM., NakanoJ., SawamaY., MonguchiY. and SajikiH., Mechanism study of copper-mediated one-pot reductive amination of aryl halides using trimethylsilyl azide, The Journal of Organic Chemistry78(18) (2013), 8980–8985.
3.
PinneyK.G. and KatzenellenbogenJ.A., Synthesis of a tetrafluoro-substituted aryl azide and its protio analog as photoaffinity labeling reagents for the estrogen receptor, The Journal of Organic Chemistry56(9) (1991), 3125–3133.
4.
GrunbeckA. and SakmarT.P., Probing G Protein-Coupled Receptor Ligand Interactions with Targeted Photoactivatable Cross-Linkers, Biochemistry52(48) (2013), 8625–8632.
5.
ThankamonyR.L., HwangJ.M. and KimT.H., Azide-assisted terminal crosslinking of ionomeric blocks: Effects on morphology and proton conductivity, Journal of Membrane Science392 (2012), 58–65.
6.
ZhangJ., KuznetsovA.M., MedvedevI.G., ChiQ., AlbrechtT., JensenP.S. and UlstrupJ., Single-molecule electron transfer in electrochemical environments, Chemical reviews108(7) (2008), 2737–2791.
7.
ZareiA., One-pot, efficient, and regioselective syntheses of 1, 4-disubstituted 1, 2, 3-triazoles using aryldiazonium silica sulfates in water, Tetrahedron Letters53(38) (2012), 5176–5179.
8.
D’AnnaF., MarulloS. and NotoR., Ionic liquids/[bmim][N3] mixtures: promising media for the synthesis of aryl azides by SNAr, The Journal of Organic Chemistry73(16) (2008), 6224–6228.
9.
TaoC.Z., CuiX., LiJ., LiuA.X., LiuL. and GuoQ.X., Copper-catalyzed synthesis of aryl azides and 1-aryl-1, 2, 3-triazoles from boronic acids, Tetrahedron letters48(20) (2007), 3525–3529.
10.
ZhuW. and MaD., Synthesis of aryl azides and vinyl azides via proline-promoted CuI-catalyzed coupling reactions, Chemical Communications2004(7), 888–889.
11.
AndersenJ., MadsenU., BjoerklingF. and LiangX., Rapid synthesis of aryl azides from aryl halides under mild conditions, Synlett2005(14) (2005), 2209–2213.
12.
ZhaoH., FuH. and QiaoR., Copper-catalyzed direct amination of ortho-functionalized haloarenes with sodium azide as the amino source, The Journal of Organic Chemistry75(10) (2010), 3311–3316.
13.
QinZ., KastratiI., ChandrasenaR.E., LiuH., YaoP., PetukhovP.A., BoltonJ.L. and ThatcherG.R., Benzothiophene selective estrogen receptor modulators with modulated oxidative activity and receptor affinity, Journal of Medicinal Chemistry50(11) (2007), 2682–2692.
14.
MarkiewiczJ.T., WiestO. and HelquistP., Synthesis of primary aryl amines through a copper-assisted aromatic substitution reaction with sodium azide, The Journal of Organic Chemistry75(14) (2010), 4887–4890.
15.
KarimzadehM., NiknamK., ManouchehriN. and TarokhD., A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a Cu 2 O–CuO–Cu–C nanocomposite, RSC Advances8(45) (2018), 25785–25793.
16.
HajipourA.R. and MohammadsalehF., Synthesis of aryl azides from aryl halides promoted by Cu2O/tetraethylammonium prolinate, Tetrahedron Letters55(50) (2014), 6799–6802.
17.
LankeS.R. and BhanageB.M., Copper bis (2, 2, 6, 6-Tetramethyl-3, 5-heptanedionate)–Catalyzed Coupling of Sodium Azide with Aryl Iodides/Boronic Acids to Aryl Azides or Aryl Amines, Synthetic Communications44(3) (2014), 399–407.
18.
GrimesK.D., GupteA. and AldrichC.C., Copper (II)-catalyzed conversion of aryl/heteroaryl boronic acids, boronates, and trifluoroborates into the corresponding azides: substrate scope and limitations, Synthesis2010(9) (2010), 1441.
19.
KutonovaK.V., TrusovaM.E., PostnikovP.S., FilimonovV.D. and ParelloJ., A simple and effective synthesis of aryl azides via arenediazonium tosylates, Synthesis45(19) (2013), 2706–2710.
20.
NematiF. and ElhampourA., Cellulose sulphuric acid as a biodegradable catalyst for conversion of aryl amines into azides at room temperature under mild conditions, Journal of Chemical Sciences124(4) (2012), 889–892.
21.
HajipourA.R., KaMorteza and SirousG., letter Selective Azidation of Aryl Halides to Aryl Azides Promoted by Proline and CuFeO2, Synlett25(20) (2014), 2903–2907.
