37887-99-3Relevant academic research and scientific papers
A new method for stereoselective bromination of stilbene and chalcone in a water suspension medium
Tanaka, Koichi,Shiraishi, Ryusukc,Toda, Fumio
, p. 3069 - 3070 (1999)
Bromination reactions of (E)-stilbene and (E)-chalcone in a water suspension medium proceeded efficiently and stereoselectively, and the reaction products were collected easily by filtration. The Royal Society of Chemistry 1999.
Catalyst-Free 1,2-Dibromination of Alkenes Using 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) as a Bromine Source
Wang, Lei,Zhai, Lele,Chen, Jinyan,Gong, Yulin,Wang, Peng,Li, Huilin,She, Xuegong
supporting information, p. 3177 - 3183 (2022/02/23)
A direct 1,2-dibromination method of alkenes is realized using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as a bromine source. This reaction proceeds under mild reaction conditions without the use of a catalyst and an external oxidant. Various sorts of alkene substrates are transformed into the corresponding 1,2-dibrominated products in good to excellent yields with broad substrate scope and exclusive diastereoselectivity. This method offers a green and practical approach to synthesize vicinal dibromide compounds.
Dibrominated addition and substitution of alkenes catalyzed by Mn2(CO)10
Chan, Albert S. C.,Jiang, Yi,Meng, Shanshui,Song, Xianheng,Zhang, Hong,Zou, Yong
supporting information, p. 13385 - 13388 (2021/12/17)
A practical method for the dibromination of alkenes without using molecular bromine is consistently appealing in organic synthesis. Herein, we report Mn-catalyzed dibrominated addition and substitution of alkenes only with N-bromosuccinimide, producing a variety of synthetically valuable dibrominated compounds in moderate to high yields. This journal is
Dibromination of alkenes with LiBr and H2O2 under mild conditions
Martins, Nayara Silva,Alberto, Eduardo E.
supporting information, p. 161 - 167 (2017/12/28)
Electron-rich and electron-poor alkenes, and alkenes bearing protecting groups can be efficiently and stereoselectively converted to trans-dibromides using LiBr/H2O2 and AcOH as a proton source in 1,4-dioxane. For most substrates addition of 0.1 mol% of PhTeTePh enhances the reaction rate and the yield of the products. Experimental data suggest that the brominating agent prepared in situ is molecular bromine and that LiBr assists the activation of H2O2 allowing bromination to occur using AcOH as a mild proton source in uncatalyzed experiments. Scale-up is feasible: 10.0 mmol of 1-octene was quantitatively converted to 1,2-dibromooctene in one hour of reaction at room temperature.
Four-component reaction leading to highly functionalized sulfoalkoxy carbonyl compounds
Sohail, Muhammad,Zhang, Yixin,Sun, Guangwei,Guo, Xin,Liu, Wujun,Liu, Chang,Zhao, Zongbao K.
supporting information, p. 4774 - 4777 (2015/03/18)
A facile regio- and diastereoselective four-component protocol has been developed involving an α,β-unsaturated carbonyl compound, a cyclic ether, a sulfonic acid and a halogen reagent to access highly anti-α-bromo-β-sulfoalkoxyl carbonyl derivatives. Some of these products have high toxicity against human chronic myeloid leukemia cells.
Halocarbocyclization versus dihalogenation: Substituent directed iodine(iii) catalyzed halogenations
Stodulski, Maciej,Goetzinger, Alissa,Kohlhepp, Stefanie V.,Gulder, Tanja
supporting information, p. 3435 - 3438 (2014/03/21)
The nucleophilicity of the substituents in iodobenzene pre-catalysts have a huge impact on product selectivity in iodine(iii) triggered halogenations, steering the reactivity from solely carbocyclizations towards dihalogenations. Utilizing this catalyst-dependent reactivity a diastereo- and chemoselective dihalogenation method was established allowing the conversion of structurally and electronically diverse unsaturated compounds in excellent yields.
Brominations with Pr4NBr9 as a solid reagent with high reactivity and selectivity
Beck, Thorsten M.,Haller, Heike,Streuff, Jan,Riedel, Sebastian
, p. 740 - 747 (2014/04/03)
Tetrapropylammonium nonabromide (Pr4NBr9) is introduced as a room-temperature solid reagent for rapid bromination reactions of various substrates. The reagent exhibits reactivity similar to that of elemental bromine, but shows higher selectivity and it is easier and safer to store and to handle. Georg Thieme Verlag Stuttgart · New York.
I2O5-mediated bromohydroxylation and dibromination of olefins using KBr in water
Wang, Yajun,Wang, Jinxi,Xiong, Yun,Liu, Zhong-Quan
supporting information, p. 2734 - 2737 (2014/05/06)
An efficient and green bromohydroxylation and dibromination of various olefins mediated by I2O5 has been developed in this work. A series of olefins gave the corresponding α-bromo-alcohols and dibromides as the major products using KBr as the brominating reagent in aqueous medium at room temperature. The diastereo- and regio-selectivities are extremely high.
Direct sustainable bromination of alkenes in aqueous media and basic ionic liquids
Primerano, Patrizia,Cordaro, Massimiliano,Scala, Angela
, p. 4061 - 4063 (2013/07/25)
Electron-rich and electron-poor alkenes have been dibrominated using a rapid and sustainable procedure. The reactions were conducted in aqueous medium and basic ionic liquids which catalyzed the direct addition of bromine. The protocol leads to remarkable results, high yields under mild conditions, complete chemo- and stereo-selectivity and allows the recycling of ionic liquids, reducing costs, and environmental impact.
Aqueous Et4NBrO3/KBr as a versatile and environmentally benign source of bromine for the selective trans-bromination of alkenes
Das, Pranab Jyoti,Sarkar, Sudeshna
, p. 802 - 806 (2013/07/26)
An aqueous solution of tetraethyl ammonium bromate and potassium bromide is found to be an environmentally benign source of bromine at ambient temperature. This reagent is used for selective trans-dibromination of several substituted alkenes. The reaction conditions are mild and the yield of the products are high and other possible by-products such as bromohydrin formation and aromatic substitution have not been observed.
