69352-05-2Relevant articles and documents
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
supporting information, 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.
Synthesis, Characterization, and Reactivity of a Hypervalent-Iodine-Based Nitrooxylating Reagent
Calvo, Roxan,Katayev, Dmitry,Le Tellier, Antoine,Nater, Darryl,Nauser, Thomas,Rombach, David
supporting information, p. 17162 - 17168 (2020/07/31)
Herein, the synthesis and characterization of a hypervalent-iodine-based reagent that enables a direct and selective nitrooxylation of enolizable C?H bonds to access a broad array of organic nitrate esters is reported. This compound is bench stable, easy-
Synthesis, Characterization, and Reaction of a Both Inter- and Intramolecularly Coordinated Pseudocyclic Iodosylbenzene–Trifluoroacetic Acid Complexes
Yudasaka, Masaharu,Maruyama, Toshifumi,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika
, p. 550 - 556 (2018/02/09)
An ortho-substituted ether-oxygen-coordinated pseudocyclic iodosylbenzene-trifluoroacetic acid (pcISB-TFA) complex was synthesized and characterized by X-ray crystallographic analysis. TFA suppresses the disproportionation by both coordination of the oxygen atom to the iodine(III) center through secondary bonding and by hydrogen bonding to the oxygen anion. This bench-stable reagent is highly soluble in common organic solvents and reacts with various organic substrates under mild reaction conditions to give the corresponding products in good yields.
