135147-69-2Relevant academic research and scientific papers
A VERSATILE SYNTHESIS OF VICINAL DIAZIDES USING HYPERVALENT IODINE
Moriarty, Robert M.,Khosrowshahi, Jaffar S.
, p. 2809 - 2812 (1986)
A convenient synthesis of vicinal diazides from olefins using C6H5IO/HOAc/NaN3 is described.A mechanism is proposed which accounts for the stereochemical outcome.
Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp3)-H Bonds with Zhdankin’s λ3-Azidoiodane
Day, Craig S.,Fawcett, Alexander,Chatterjee, Ruchira,Hartwig, John F.
supporting information, p. 16184 - 16196 (2021/10/12)
An in-depth study of the mechanism of the azidation of C(sp3)-H bonds with Zhdankin’s λ3-azidoiodane reagent catalyzed by iron(II)(pybox) complexes is reported. Previously, it was shown that tertiary and benzylic C(sp3)-H bonds of a range of complex molecules underwent highly site-selective azidation by reaction with a λ3-azidoiodane reagent and an iron(II)(pybox) catalyst under mild conditions. However, the mechanism of this reaction was unclear. Here, a series of mechanistic experiments are presented that reveal critical features responsible for the high selectivity and broad scope of this reaction. These experiments demonstrate the ability of the λ3-azidoiodane reagent to undergo I-N bond homolysis under mild conditions to form λ2-iodanyl and azidyl radicals that undergo highly site-selective and rate-limiting abstraction of a hydrogen atom from the substrate. The resultant alkyl radical then combines rapidly with a resting state iron(III)-azide complex, which is generated by the reaction of the λ3-azidoiodane with the iron(II)(pybox) complex, to form the C(sp3)-N3bond. This mechanism is supported by the independent synthesis of well-defined iron complexes characterized by cyclic voltammetry, X-ray diffraction, and EPR spectroscopy, and by the reaction of the iron complexes with alkanes and the λ3-azidoiodane. Reaction monitoring and kinetic studies further reveal an unusual effect of the catalyst on the rate of formation of product and consumption of reactants and suggest a blueprint for the development of new processes leading to late-stage functionalization of C(sp3)-H bonds.
Diazide compound preparation method
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Paragraph 0111-0112; 0114; 0118; 0120; 0130-0133; 0243-0245, (2019/05/16)
The present invention discloses a diazide compound preparation method, which comprises: carrying out a reaction on a compound containing a carbon-carbon double bond and an azidating reagent in the presence of a catalyst and a free radical initiator to prepare the diazide compound. According to the present invention, the method has advantages of simple operation, environmental protection, mild reaction condition, wide substrate range and good functional-group tolerance, wherein the reaction can be efficiently performed in organic solvents and water systems.
Visible-light activated metal catalyst-free vicinal diazidation of olefins with sulfonium iodate(i) species
Reddy, Thurpu Raghavender,Rao, Dodla Sivanageswara,Kashyap, Sudhir
supporting information, p. 2833 - 2836 (2019/03/17)
A visible light-induced vicinal diazidation of various alkenes using stable sulfonium bis(acetoxy)iodate(i) and sodium azide as a radical precursor is described. The trimethylsulfonium [bis(azido)iodate(i)] species, intrinsically generated in situ, demonstrated unprecedented reactivity toward CC π bond-promoting selective azidation under photochemical conditions without any photoredox or metal catalyst. The visible-light stimulated diazidation reaction provides a convenient and straightforward approach to highly prevalent vicinal nitrogen scaffolds of myriad therapeutic importance.
Copper-Catalyzed Ligand-Free Diazidation of Olefins with TMSN3 in CH3CN or in H2O
Zhou, Huan,Jian, Wujun,Qian, Bo,Ye, Changqing,Li, Daliang,Zhou, Jing,Bao, Hongli
supporting information, p. 6120 - 6123 (2017/11/27)
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.
Stereoisomeric Dichloroplatinum(II) Complexes, Part I: Synthesis
Mueller, Richard,Gust, Ronald,Klement, Ulrich,Schoenenberger, Helmut
, p. 2381 - 2389 (2007/10/02)
Various erythro- and threo-configurated dichloroplatinum(II) complexes were synthesized with the hydroxy group located in either the 2-, 3-, or 4-position of the phenyl ring (38-40).The diastereoisomeric 1-(3-
