82668-86-8Relevant academic research and scientific papers
A Free-Radical Reduction and Cyclization of Alkyl Halides Mediated by FeCl2
Pulikottil, Feba Thomas,Pilli, Ramadevi,Murugesan, Vetrivelan,Krishnan, Chandu G.,Rasappan, Ramesh
, p. 2438 - 2442 (2019/04/30)
Iron mediated catalytic reactions are of great interest in the field of organic synthesis because they are economic and naturally abundant. However, the use of iron catalyst in the field of free radical cyclization or reduction of alkyl halides remains limited. Here we describe the use of an unprecedented combination of iron and zinc in the reduction and 5-exo-trig radical cyclization of alkyl halides under mild condition in the absence of added ligands or additives. The method is distinguished by its wide scope, functional group tolerance and the use of 1,4-cyclohexadiene as the source of hydrogen, which aids easy purification.
Iron(II) catalyzed reductive radical cyclization reactions of bromoacetals in the presence of NaBH4: optimization studies and mechanistic insights
Kyne, Sara H.,Lévêque, Christophe,Zheng, Shiwen,Fensterbank, Louis,Jutand, Anny,Ollivier, Cyril
supporting information, p. 7727 - 7737 (2016/11/18)
5-Exo-trig radical reductive cyclization reactions of bromoacetals are catalyzed by iron in the presence of the reducing agent NaBH4. Both iron(II) and iron(III) were found to effectively mediate these reactions. As shown by cyclic voltammetry, iron(III) can be reduced to an iron(II) precatalyst before passing through an identical reaction mechanism in which monoelectronic activation of the substrate would occur by an anionic hydridoiron(I) complex. Further studies have established that both the substrate (iodo- vs bromo-derivative) and the precatalytic mixture are decisive in determining the reaction outcome.
Indium hydride: A novel radical initiator in the reduction of organic halides with tributyltin hydride
Inoue, Katsuyuki,Sawada, Akemi,Shibata, Ikuya,Baba, Akio
, p. 4661 - 4663 (2007/10/03)
Dichloroindium hydride (Cl2InH), which was generated in situ by transmetallation between tributyltin hydride and indium trichloride, acted as a novel radical initiator for the reduction of organic halides with tributyltin hydride. The reaction was revealed to proceed through a radical process under non-oxygen conditions at room temperature, and to be applicable to intramolecular radical cyclizations.
Indirect Electroreductive Radical Cyclization of Halogeno Ethers using Nickel(II) Complexes as Electron-transfer Catalysts
Ozaki, Shigeko,Matsushita, Hidenori,Ohmori, Hidenobu
, p. 1120 - 1122 (2007/10/02)
Indirect electrochemical radical cyclization of halogeno ethers is achieved under mild conditions using nickel(II) complexes as electron-transfer catalysts.
The Reaction of Bis(dimethylglyoximato)(pyridine)cobalt(I), Cobaloxime(I), with 2-(Allyloxy)ethyl Halides and the Photolysis of the Resulting Organo-cobaloximes
Okabe, Masami,Tada, Masaru
, p. 1498 - 1503 (2007/10/02)
The reactions of 2-(allyloxy)ethyl halides with cobaloxime(I) gave (tetrahydro-3-furanyl)methylcobaloximes via an electron transfer from cobaloxime(I) to the halides to give radical anions.The rupture of a halide ion to give an organic radical and the ring closure to give a (tetrahydro-3-furanyl)methyl radical are followed by the radical coupling between the organic radical and the cobaloxime(II).The structures of the organocobaloximes were determined by the analyses of the photolysis products under aerobic or anaerobic conditions.
