28988-98-9

Upstream product

• 300-57-2 allylbenzene 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 100-58-3 phenylmagnesium bromide 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 55510-08-2 1-bromo-3-phenylpropan-2-yl acetate 

Downstream Products

• 20772-12-7 1-bromo-3-phenyl-2-propanone 
• 102670-69-9 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-hydroxy-3-phenyl-propoxy)-benzamide 
• 135608-75-2 benzyl carbamate 

Relevant academic research and scientific papers

The Discovery of a Palladium(II)-Initiated Borono-Catellani Reaction

Reported is a novel palladium(II)-initiated Catellani-type reaction that utilizes widely accessible aryl boronic acids as the substrates instead of aryl halides, thereby greatly expanding the existing scope of this powerful transformation. This borono-Catellani reaction was promoted by cooperative catalysis between Pd(OAc)2 and the inexpensive 5-norbornene-2-carbonitrile. Practicality is the striking feature of the reaction: it is run open to air at ambient temperature and no phosphine ligand is needed. This mild, chemoselective, and scalable protocol is compatible with a large range of readily available functionalized aryl boronic acids and bromides, as well as terminating olefins (50 examples, 39–97 % yields). Moreover, the orthogonal reactivity between the borono-Catellani and classical Catellani reaction was demonstrated. This work is expected to open new avenues for developing novel Catellani-type reactions.

Alkene, Bromide, and ROH – How To Achieve Selectivity? Electrochemical Synthesis of Bromohydrins and Their Ethers

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

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.

Halofunctionalization of alkenes by vanadium chloroperoxidase from: Curvularia inaequalis

The vanadium-dependent chloroperoxidase from Curvularia inaequalis is a stable and efficient biocatalyst for the hydroxyhalogenation of a broad range of alkenes into halohydrins. Up to 1 200 000 TON with 69 s-1 TOF were observed for the biocatalyst. A bienzymatic cascade to yield epoxides as reaction products is presented.

Synthesis and biological evaluation of 5-substituted and 4,5-disubstituted-2-arylamino oxazole TRPV1 antagonists

The synthesis and structure-activity relationships of a series of 5-monosubstituted and 4,5-disubstituted 2-arylaminooxazoles as novel antagonists of the transient receptor potential vanilloid 1 (TRPV1) receptor are described. The 7-hydroxy group of the t

Monobromoborane-dimethyl sulfide - A highly promising reagent for the regio- and chemoselective brominative cleavage of terminal epoxides into vicinal bromohydrins

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.

A highly regio- and chemoselective synthesis of vicinal bromohydrins by ring opening of terminal epoxides with dibromoborane-dimethyl sulfide

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.

A bimetallic palladium(II) catalyzed synthesis of 1,2-dibromo compounds

A bimetallic palladium(II) catalyst containing a triketone ligand and a bridging dinitrogen ligand oxidizes aromatic and cyclic aliphatic olefins in bromide-containing aqueous-THF to 1,2-dibromo compounds and bromohydrins. With aromatic olefins, the 1,2-dibromo products were obtained in a 70-80% yield and the bromohydrins in a 10-15% yield; this observation is opposition to that obtained in chloride containing medium where the chlorohydrin product predominates. The oxidation of 2,3-dihydrofuran gave trans-2,3- dibromotetrahydrofuran, 3-oxotetrahydrofuran, and 3-bromo-2- hydroxytetrahydrofuran in relative yields of 75%, 15%, and 10%, respectively. On the other hand, the oxidation of cyclopentene and cyclohexene affords only trans-1,2-dibromo products in about 90% yield. The stereochemistry is consistent with an anti-at-tack of bromide followed by decomposition involving attack of bromide from the coordination sphere of the Pd(II). The procedure outlined here is a convenient method for the one step synthesis of 1,2-dibromides.

Dimethoxyboron bromide - A new, efficient, regio- and chemoselective reagent for the conversion of terminal epoxides into bromohydrins

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).

Pseudomonas Lipases as Catalysts in Organic Synthesis: Specificity of Lipoprotein Lipase

Described are the structural features of the substrates accepted by lipoprotein lipase from Pseudomonas aeruginosa which can serve as the rules for interpreting and predicting the specificity of this enzyme.