22710-73-2Relevant articles and documents
Iodoazidation of Alkenes by Using Iodine Pentafluoride-Pyridine-Hydrogen Fluoride and Trimethylsilyl Azide
Hiraoka, Tatsuki,Yano, Shohei,Hara, Shoji
, p. 1353 - 1358 (2016)
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.
Palladium-Catalyzed Intermolecular Oxidative Diazidation of Alkenes
Peng, Haihui,Yuan, Zheliang,Chen, Pinhong,Liu, Guosheng
, p. 876 - 880 (2017/06/27)
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
Sun, Xiang,Li, Xinyao,Song, Song,Zhu, Yuchao,Liang, Yu-Feng,Jiao, Ning
supporting information, p. 6059 - 6066 (2015/05/27)
(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.