22710-73-2

Upstream product

• 100-42-5 styrene 
• 160732-56-9 1-azido-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 4648-54-8 trimethylsilylazide 

Downstream Products

• 5700-56-1 1,2-diaminophenylethane 
• 138373-91-8 1-azido-1-phenyl-2-(N-tert-butoxycarbonylamino)ethane 
• 138457-47-3 1-azido-2-phenyl-2-(N-tert-butoxycarbonylamino)ethane 
• 96788-10-2 1-azido-1-phenyl-2-aminoethane 
• 129687-45-2 1-phenylethane-1,2-diaminium ditosylate 
• 95006-06-7 N,N'-(phenyl-ethanediyl)-bis-benzamide 

Relevant academic research and scientific papers

Iodoazidation of Alkenes by Using Iodine Pentafluoride-Pyridine-Hydrogen Fluoride and Trimethylsilyl Azide

Iodoazidation of alkenes was carried out by using iodine pentafluoride-pyridine-hydrogen fluoride and trimethylsilyl azide. In the reactions of terminal alkenes, anti-Markovnikov products were formed selectively. Cyclohexene gave a mixture of cis- and trans-adducts. These results suggest the involvement of radical species in the reaction.

Copper-Catalyzed Ligand-Free Diazidation of Olefins with TMSN3 in CH3CN or in H2O

An environmentally benign, copper-catalyzed diazidation of a broad range of olefins, including vinylarenes, unactivated alkenes, allene, and dienes, under mild conditions with TMSN3 (trimethylazidosilane) as azido source, has been developed. This reaction can be carried out in organic solvent or in aqueous solution where water is the sole solvent. The functional group compatibility of this reaction is good, which is proved by late-stage functionalizations of complex substrates.

Palladium-Catalyzed Intermolecular Oxidative Diazidation of Alkenes

A palladium-catalyzed oxidative vicinal diazidation of alkenes has been developed, in which TMSN3 was used as azide source. Both styrenes and unactivated alkenes are suitable for this reaction. And trans-alkyldiazides were obtained as major products from cyclic alkenes with moderate to good diastereoselectivities. This reaction afforded an efficient way for the synthesis of useful 1,2-diamines after hydrogenation.

Mn-Catalyzed Highly Efficient Aerobic Oxidative Hydroxyazidation of Olefins: A Direct Approach to β-Azido Alcohols

(Chemical Equation Presented). An efficient Mn-catalyzed aerobic oxidative hydroxyazidation of olefins for synthesis of β-azido alcohols has been developed. The aerobic oxidative generation of azido radical employing air as the terminal oxidant is disclosed as the key process for this transformation. The reaction is appreciated by its broad substrate scope, inexpensive Mn-catalyst, high efficiency, easy operation under air, and mild conditions at room temperature. This chemistry provides a novel approach to high value-added β-azido alcohols, which are useful precursors of aziridines, β-amino alcohols, and other important N- and O-containing heterocyclic compounds. This chemistry also provides an unexpected approach to azido substituted cyclic peroxy alcohol esters. A DFT calculation indicates that Mn catalyst plays key dual roles as an efficient catalyst for the generation of azido radical and a stabilizer for peroxyl radical intermediate. Further calculation reasonably explains the proposed mechanism for the control of C-C bond cleavage or for the formation of β-azido alcohols.

Copper-Catalyzed Vicinal Oxyazidation and Diazidation of Styrenes under Mild Conditions: Access to Alkyl Azides

A novel and efficient copper-catalyzed oxyazidation and diazidation of styrenes is described. The stable azidoiodine(III) reagent is used as an efficient azide radical source in this reaction. A variety of synthetically useful functional groups are compat