66820-58-4Relevant academic research and scientific papers
Monobromoborane-dimethyl sulfide - A highly promising reagent for the regio- and chemoselective brominative cleavage of terminal epoxides into vicinal bromohydrins
Roy, Chandra D.,Brown, Herbert C.
, p. 139 - 145 (2007)
Monobromoborane?dimethyl sulfide (BH2Br?SMe2) is a highly regio- and chemoselective reagent useful for the brominative cleavage of the epoxy moiety into bromohydrins in the presence of alkenes, alkynes, ethers, acetals, ketals, and acetonides at 0°C, besides being an excellent hydroborating reagent. Several reactive functional groups, such as chloride, ketones, esters, nitriles, nitros, and thioethers, have been accommodated during such transformations. Although the reduction of acetophenone was completely suppressed at ?25°C, 4-chlorobenzaldehyde still underwent 12?13% reduction of an aldehydic group. CSIRO 2007.
Alkene, Bromide, and ROH – How To Achieve Selectivity? Electrochemical Synthesis of Bromohydrins and Their Ethers
Bityukov, Oleg V.,Nikishin, Gennady I.,Terent'ev, Alexander O.,Vil', Vera A.
supporting information, p. 3070 - 3078 (2021/05/10)
Bromohydrins and their ethers were electrochemically synthesized via hydroxy- and alkoxybromination of alkenes using potassium bromide and water or alcohols. High selectivity of bromohydrins formation was achieved only with the use of DMSO as the solvent and an acid as the additive. The proposed combination of starting reagents, additives, and solvents allowed to form bromohydrins or their ethers selectively despite the variety of side-products (epoxides, dibromides, diols). Bromohydrins were obtained in high yields, up to 96%, with a broad substrate scope in an undivided electrochemical cell equipped with glassy carbon and platinum electrodes at high current density. (Figure presented.).
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.
Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: Stereoconvergent suzuki reactions of racemic acylated halohydrins
Owston, Nathan A.,Fu, Gregory C.
supporting information; experimental part, p. 11908 - 11909 (2010/11/04)
A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with alkylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.
Direct asymmetric bromination of aldehydes catalyzed by a binaphthyl-based secondary amine: Highly enantio- and diastereoselective one-pot synthesis of bromohydrins
Kano, Taichi,Shirozu, Fumitaka,Maruoka, Keiji
supporting information; experimental part, p. 7590 - 7592 (2010/11/18)
One-pot stereoselective synthesis of bromohydrins as a useful chiral building block was achieved by the reaction of Grignard reagents with optically active α-bromoaldehydes, which were in situ generated by direct asymmetric bromination of aldehydes cataly
A highly regio- and chemoselective synthesis of vicinal bromohydrins by ring opening of terminal epoxides with dibromoborane-dimethyl sulfide
Roy, Chandra D.,Brown, Herbert C.
, p. 1608 - 1613 (2007/10/03)
Dibromoborane-dimethyl sulfide (BHBr2-SMe2) displays high degrees of chemo- and regioselectivity during the brominative cleavage of the epoxy group into vicinal bromohydrins in the presence of alkene, alkyne, allene, ether, acetal and acetonide, besides its hydroborating ability. Several reducible functional groups, such as chloride, aldehyde, ketone, azide, ester, nitrile and tert-amino ester, have been successfully accommodated during the epoxide opening process.
Dimethoxyboron bromide - A new, efficient, regio- and chemoselective reagent for the conversion of terminal epoxides into bromohydrins
Roy, Chandra D.,Brown, Herbert C.
, p. 639 - 641 (2007/10/03)
Dimethoxyboron bromide, (MeO)2BBr, easily prepared in excellent yield from boron tribromide and trimethyl borate, is a new, efficient, regio- and chemoselective reagent useful for the halogenative cleavage of compounds containing epoxy groups into vicinal bromohydrins in the presence of ether, acetal, ketal, N-oxide, and sulfoxide groups, at low temperatures (-78°C).
Synthesis and resolution of the novel appetite suppressant 2-benzylmorpholine, a nonstimulant isomer of phenmetrazine
Brown,Forster,Foubister,Stribling
, p. 797 - 799 (2007/10/02)
The synthesis of 2-benzylmorpholine from allylbenzene together with its resolution into its (+)- and (-)-enantiomers is reported. Oral dosing of the racemate to dogs caused appetite suppression with an ED50 of 3 and 5.5 mg kg-1 at 1 and 2 h, re
