32730-32-8Relevant articles and documents
Synthesis of Benzoisoselenazolone Derivatives by Nickel-Catalyzed Dehydrogenative Direct Selenation of C(sp2)-H Bonds with Elemental Selenium in Air
Iwasaki, Masayuki,Miki, Natsumi,Tsuchiya, Yuta,Nakajima, Kiyohiko,Nishihara, Yasushi
, p. 1092 - 1095 (2017)
Nickel-catalyzed direct selenation of benzamides bearing an 8-quinolyl auxiliary with elemental selenium provides benzoisoselenazolones in good yield via carbon-selenium and nitrogen-selenium bond formation under aerobic conditions. In addition to aryl C-
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.
, p. 5680 - 5682 (2014)
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
Bromoiodinanes with an I(III)-Br bond: Preparation, X-ray crystallography and reactivity as electrophilic brominating agents
Braddock, D. Christopher,Cansell, Gemma,Hermitage, Stephen A.,White, Andrew J. P.
, p. 1442 - 1444 (2006)
Bromoiodinanes - conveniently and directly prepared from iodobenzenecarbinols and N-bromosuccinimide, and characterised for the first time crystallographically - act as electrophilic bromine donors. The Royal Society of Chemistry 2006.
H2O2 Production at Low Overpotentials for Electroenzymatic Halogenation Reactions
Bormann, Sebastian,van Schie, Morten M. C. H.,De Almeida, Tiago Pedroso,Zhang, Wuyuan,St?ckl, Markus,Ulber, Roland,Hollmann, Frank,Holtmann, Dirk
, p. 4759 - 4763 (2019)
Various enzymes utilize hydrogen peroxide as an oxidant. Such “peroxizymes” are potentially very attractive catalysts for a broad range of oxidation reactions. Most peroxizymes, however, are inactivated by an excess of H2O2. The electrochemical reduction of oxygen can be used as an in situ generation method for hydrogen peroxide to drive the peroxizymes at high operational stabilities. Using conventional electrode materials, however, also necessitates significant overpotentials, thereby reducing the energy efficiency of these systems. This study concerns a method to coat a gas-diffusion electrode with oxidized carbon nanotubes (oCNTs), thereby greatly reducing the overpotential needed to perform an electroenzymatic halogenation reaction. In comparison to the unmodified electrode, with the oCNTs-modified electrode the overpotential can be reduced by approximately 100 mV at comparable product formation rates.
Amidines as potent nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
Ahmad, Simon M.,Braddock, D. Christopher,Cansell, Gemma,Hermitage, Stephen A.,Redmond, Joanna M.,White, Andrew J.P.
, p. 5948 - 5952 (2007)
(±)-iso-Amarine is a potent organocatalyst at 1 mol % loading for both the bromoacetoxylation of alkenes with added acetic acid and bromolactonisation of unsaturated carboxylic acids with stoichiometric NBS as the electrophilic bromine source. A simple br
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)
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
Fenton chemistry for Achmatowicz rearrangement
Zhao, Guodong,Liang, Lixin,Wang, Eryu,Tong, Rongbiao
, p. 3740 - 3748 (2021)
Achmatowicz rearrangement (AchR) is a very important transformation for the synthesis of various heterocyclic building blocks and natural products. Here, the discovery of Fenton chemistry for AchR using a bifunctional catalyst (FeBr2 or CeBrsu
Chalcogen-Bonding Catalysis with Telluronium Cations
Aubert, Emmanuel,Mamane, Victor,Pale, Patrick,Weiss, Robin
supporting information, p. 19281 - 19286 (2021/07/25)
Chalcogen bonding results from non-covalent interactions occurring between electrodeficient chalcogen atoms and Lewis bases. Among the chalcogens, tellurium is the strongest Lewis acid, but Te-based compounds are scarcely used as organocatalysts. For the first time, telluronium cations demonstrated impressive catalytic properties at low loadings in three benchmark reactions: the Friedel–Crafts bromination of anisole, the bromolactonization of ω-unsaturated carboxylic acids and the aza-Diels–Alder between Danishefsky's diene and imines. The ability of telluronium cations to interact with a Lewis base through chalcogen bonding was demonstrated on the basis of multi-nuclear (17O, 31P, and 125Te) NMR analysis and DFT calculations.
Electrochemical bromofunctionalization of alkenes in a flow reactor
Seitz, Jakob,Wirth, Thomas
supporting information, p. 6892 - 6896 (2021/08/20)
The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste production are the most persisting problems of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, thein situgeneration of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted to their corresponding dibromides, bromohydrines, bromohydrin ethers and cyclized products in good to excellent yields.
New syntheses of haloketo acid methyl esters and their transformation to halolactones by reductive cyclization
China, H.,Dohi, T.,Fujitake, M.,Kageyama, N.,Kikushima, K.,Yatabe, H.
, p. 1804 - 1810 (2020/10/16)
A new method for haloketo acid methyl ester synthesis on the basis of the ring-opening of cyclic α,β-unsaturated ketones followed by halogenation under mild conditions is reported. Di- and tri-haloketo acid methyl esters are conveniently synthesized via the hydrolytic ring-opening reaction through this method. Halolactones were readily obtained from these haloketo acid methyl esters by reductive cyclization employing NaBH4 and trifluoroacetic acid. Derivatizations of the obtained halolactone utilizing the exo-halomethylene moiety were also demonstrated.
