87629-98-9Relevant academic research and scientific papers
Hexafluoroisopropanol-Promoted Haloamidation and Halolactonization of Unactivated Alkenes
Qi, Chenxiao,Force, Guillaume,Gandon, Vincent,Leb?uf, David
supporting information, p. 946 - 953 (2020/12/01)
Pyrrolidine and piperidine derivatives bearing halide functional groups are prevalent building blocks in drug discovery as halides can serve as an anchor for post-modifications. In principle, one of the simplest ways to build these frameworks is the haloa
A Highly Efficient Method for the Bromination of Alkenes, Alkynes and Ketones Using Dimethyl Sulfoxide and Oxalyl Bromide
Ding, Rui,Li, Jiaqi,Jiao, Wenyi,Han, Mengru,Liu, Yongguo,Tian, Hongyu,Sun, Baoguo
, p. 4325 - 4335 (2018/11/21)
The pairing of DMSO and oxalyl bromide is reported as a highly efficient brominating reagent for various alkenes, alkynes and ketones. This bromination approach demonstrates remarkable advantages, such as mild conditions, low cost, short reaction times, provides excellent yields in most cases and represents a very attractive alternative for the preparation of dibromides and α-bromoketones.
Esterification of the olefine acid bromine in a preparation method (by machine translation)
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Paragraph 0010; 0011, (2018/01/11)
The invention relates to shown in the following formula of esterification of the olefine acid bromine in preparation method: The method comprises the steps: in - 78 °C first will be dimethyl sulfoxide (1.5 eq) methylene dichloride solution of instillment
Vanadium (V) oxide mediated bromolactonization of alkenoic acids
Campbell, McKenzie L.,Rackley, Samuel A.,Giambalvo, Lauren N.,Whitehead, Daniel C.
, p. 3895 - 3902 (2015/06/02)
A full account of our recently communicated method for the V2O5 mediated bromolactonization of alkenoic acids is presented. Here we describe the extensive evaluation of the metal oxide catalyst, terminal oxidant, halide source, solvent system, and reaction temperature that resulted in optimal conditions employing 0.05 equiv V2O5, 3 equiv urea-hydrogen peroxide complex (UHP), and 3 equiv of NH4Br in an acetone:H2O (6:1) solvent system at room temperature. Additionally, we have expanded the substrate scope of the reaction with the aim of evaluating the functional group tolerance of the transformation. Further, we present preliminary data of a related halogenation of β-diketones with our optimal conditions. Finally, we probed the role of urea in the transformation.
Oxidative oxygen-nucleophilic bromo-cyclization of alkenyl carbonyl compounds without organic wastes using alkali metal reagents in green solvent
Moriyama, Katsuhiko,Nishinohara, Chihiro,Sugiue, Toru,Togo, Hideo
, p. 85872 - 85878 (2015/11/03)
A bromo-lactonization of alkenyl carboxylic acids and a bromo-cyclization of N-allyl amides as oxygen-nucleophilic bromo-cyclization reactions were developed via the oxidative umpolung of bromide using alkali metal bromide and inorganic oxidant to provide
Bromolactonization of alkenoic acids mediated by V2O5via bromide to bromenium in situ oxidation
Campbell, McKenzie L.,Rackley, Samuel A.,Giambalvo, Lauren N.,Whitehead, Daniel C.
supporting information, p. 5680 - 5682 (2015/01/08)
An efficient protocol for the bromolactonization of alkenoic acids is presented that obviates the use of molecular bromine or exogenous bromenium sources. Vanadium (V) oxide catalyzes the in situ oxidation of bromide salts to bromenium (Br+) in
Selenium-catalyzed oxidative halogenation
Mellegaard-Waetzig, Shelli R.,Wang, Chao,Tunge, Jon A.
, p. 7191 - 7198 (2007/10/03)
Organoselenides catalyze the oxidation of halides by H2O2. Furthermore, these selenides catalyze the transfer of oxidized halogens from N-halosuccinimides to olefins and ketones. Thus, organoselenides catalyze oxidative halogenation reactions including halolactonization, α-halogenation of ketones, and allylic halogenation. The ability of selenium to undergo reversible 2e- oxidation-reduction chemistry facilitates halogenation through selenium-bound halogen intermediates.
Stereoselective synthesis of (E)-β-arylvinyl bromides by microwave-induced Hunsdiecker-type reaction
Kuang, Chunxiang,Yang, Qing,Senboku, Hisanori,Tokuda, Masao
, p. 1319 - 1325 (2007/10/03)
(E)-β-Arylvinyl bromides were readily prepared in a short reaction time (1-2 min) by microwave irradiation of the corresponding 3-arylpropenoic acids in the presence of N-bromosuccinimide and a catalytic amount of lithium acetate. Furthermore, two facile strategies for the efficient synthesis of (E)-β-bromo-4-arylethynylstyrene and (E)-β-bromo-4-arylstyrene have been developed by respectively combining Sonogashira and Suzuki coupling reaction with Hunsdiecker-type reaction. Formation of cis-α-bromo-β- lactone by microwave irradiation of cis-cinnamic acid with NBS provides a useful support for the mechanistic study of the present halodecarboxylation reaction. Georg Thieme Verlag Stuttgart.
Selenium-catalyzed halolactonization: Nucleophilic activation of electrophilic halogenating reagents
Mellegaard, Shelli R.,Tunge, Jon A.
, p. 8979 - 8981 (2007/10/03)
Diphenyl diselenide catalyzes the halolactonization of unsaturated acids with N-halosuccinimides under mild conditions. The diselenide not only accelerates the reactions, but in some cases affords regiocontrol in favor of γ-lactone products. Experiments s
