69352-04-1Relevant articles and documents
Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds
Liu, Wen,Pu, Maoping,He, Jun,Zhang, Tinghui,Dong, Shunxi,Liu, Xiaohua,Wu, Yun-Dong,Feng, Xiaoming
, 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.
Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C
Bisai, Alakesh,Das, Mrinal Kanti,De, Subhadip,Maity, Arindam,Naskar, Malay,Roy, Avishek
supporting information, p. 1679 - 1684 (2020/03/05)
Efficient oxidative direct cyanations of 3-alkyl/aryl 2-oxindoles using Cyano-1,2-BenziodoXol-3(1H)-one (CBX) (2a) have been reported under 'transition metal-free' conditions to synthesize a wide variety of 3-cyano 3-alkyl/aryl 2-oxindoles sharing an all-carbon quaternary center under additive-free conditions. The application of this process is shown by the formal total synthesis of (±)-gliocladin C (11c) in a few steps.
Radical C?H-Amination of Heteroarenes using Dual Initiation by Visible Light and Iodine
Lucchetti, Nicola,Tkacheva, Anastasia,Fantasia, Serena,Mu?iz, Kilian
, p. 3889 - 3893 (2018/09/21)
A novel light-induced C?H amination of heteroarenes can be accomplished with preformed iodine(III) reagents as the combined oxidant and nitrogen source. The reaction requires the use of a small amount of molecular iodine, which under photochemical activation generates in situ an iodine(I) reagent as the initiator of the radical amination reaction. A total of 32 examples exemplify the broad scope of the transformation. (Figure presented.).