347-90-0Relevant articles and documents
H2O2-mediated room temperature synthesis of 2-arylacetophenones from arylhydrazines and vinyl azides in water
Luo, Mengqiang,Zhang, Yaohong,Fang, Ping,Li, Yan,Qi, Chenze,Li, Yong,Shen, Runpu,Cheng, Kai,Wang, Hai
supporting information, p. 630 - 635 (2022/02/01)
An environmentally benign, cost-efficient and practical methodology for the room temperature synthesis of 2-arylacetophenones in water has been discovered. The facile and efficient transformation involves the oxidative radical addition of arylhydrazines with α-aryl vinyl azides in the presence of H2O2 (as a radical initiator) and PEG-800 (as a phase-transfer catalyst). From the viewpoint of green chemistry and organic synthesis, the present protocol is of great significance because of using cheap, non-toxic and readily available starting materials and reagents as well as amenability to gram-scale synthesis, which provides an attractive strategy to access 2-arylacetophenones.
Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds
Dong, Shunxi,Feng, Xiaoming,He, Jun,Liu, Wen,Liu, Xiaohua,Pu, Maoping,Wu, Yun-Dong,Zhang, Tinghui
, p. 11856 - 11863 (2021/08/16)
Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.
Catalyst-controlled highly selective coupling and oxygenation of olefins: A direct approach to alcohols, ketones, and diketones
Su, Yijin,Sun, Xiang,Wu, Guolin,Jiao, Ning
supporting information, p. 9808 - 9812 (2013/09/23)
Oxygen? That's radical! A method for the direct synthesis of substituted alcohols, ketones, and diketones through a catalyst-controlled highly chemoselective coupling and oxygenation of olefins has been developed. The method is simple and practical, can be switched by the selection of different catalysts, and employs molecular oxygen as both an oxidant and a reagent. Copyright