59339-58-1Relevant academic research and scientific papers
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.
Route exploration and synthesis of the reported pyridone-based PDI inhibitor STK076545
Dockendorff, Chris,Flaumenhaft, Robert,Greve, Eric,Lin, Lin,Lindeman, Sergey V.,Scartelli, Christina
, p. 6665 - 6681 (2020/09/21)
The enzyme protein disulfide isomerase (PDI) is essential for the correct folding of proteins and the activation of certain cell surface receptors, and is a promising target for the treatment of cancer and thrombotic conditions. A previous high-throughput screen identified the commercial compound STK076545 as a promising PDI inhibitor. To confirm its activity and support further biological studies, a resynthesis was pursued of the reported β-keto-amide with an N-alkylated pyridone at the α-position. Numerous conventional approaches were complicated by undesired fragmentations or rearrangements. However, a successful 5-step synthetic route was achieved using an aldol reaction with an α-pyridone allyl ester as a key step. An X-ray crystal structure of the final compound confirmed that the reported structure of STK076545 was achieved, however its lack of PDI activity and inconsistent spectral data suggest that the commercial structure was misassigned.
Regio-and stereoselective hydroxybromination and dibromination of olefins using ammonium bromide and oxone
MacHarla, Arun Kumar,Chozhiyath Nappunni, Rohitha,Nama, Narender
supporting information; experimental part, p. 1401 - 1405 (2012/04/04)
An efficient protocol for the synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio-and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov's rule, using eco-friendly, non-toxic, and stable reagents such as NH4Br and oxone in CH3CN/H2O (1:1) and CH3CN without employing catalyst in moderate to excellent yields. Bromohydrins are formed instantaneously.
Highly regio- and diastereoselective halohydroxylation of olefins: A facile synthesis of vicinal halohydrins
Zhang, Jinglei,Wang, Jie,Qiu, Zhuibai,Wang, Yang
experimental part, p. 6859 - 6867 (2011/10/02)
An efficient method for the synthesis of vicinal chlorohydrin or bromohydrin derivatives has been developed on the basis of direct halohydroxylation of various olefins with electrondonating or withdrawing substituent. The reactions were carried out under mild conditions in the presence of N-tosyl-l-threonine (NTsLT) as an acidic additive using chloramine T trihydrate, 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) or N-bromoacetamide (AcNHBr) as the halogen source, respectively, affording the corresponding vicinal halohydrins in good to high yields with excellent regio- and stereoselectivities.
Organocatalysis in the stereoselective bromohydrin reaction of alkenes
Bar, Sukanta
experimental part, p. 605 - 612 (2010/08/21)
An efficient regio- and stereo-selective (>99:1) trans-bromohydrination (bromohydroxylation and bromomethoxylation) of alkenes including α,β-unsaturated carbonyl compounds with N-bromosuccinimide (NBS) has been achieved by using 1.0 mol% of N,N'-diarylthi
Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
Agrawal, Manoj K.,Adimurthy, Subbarayappa,Ganguly, Bishwajit,Ghosh, Pushpito K.
supporting information; experimental part, p. 2791 - 2797 (2009/08/08)
A comparative evaluation was made on the syntheses of vicinal halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br-/BrO3- and I-/IO3- reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br-/BrO3- and I-/IO3-, respectively. Of the two reagents, I-/IO3- was established to be the preferred reagent for vicinal functionalization of linear alkenes and also for halo acetate preparation. However, only Br-/BrO3- was effective for vicinal functionalization of trans-stilbene and chalcones.
Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones
Hoover, Trisha R.,Groeper, Jonathan A.,Parrott II, Raleigh W.,Chandrashekar, Seshanand P.,Finefield, Jennifer M.,Dominguez, Alexandro,Hitchcock, Shawn R.
, p. 1831 - 1841 (2007/10/03)
Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric α-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good.
A simple and efficient method for regioselective and stereoselective synthesis of vicinal bromohydrins and alkoxybromides from an olefin
Phukan, Prodeep,Chakraborty, Pranita,Kataki, Dolly
, p. 7533 - 7537 (2007/10/03)
(Chemical Equation Presented) A very rapid and efficient method has been developed for the synthesis of vicinal bromohydrins and alkoxybromides directly from an olefin without any catalyst. The reaction was performed in CH 3CN-water (4:1) or alcohol using N,N-dibromo-p-toluenesulfonamide (TsNBr2) as the brominating agent. Excellent yields and regio- and stereoselectivities have been obtained. Bromohydrins are formed instantaneously, whereas formation of alkoxybromides takes 30-60 min.
Synthesis of bromo- And iodohydrins from deactivated alkenes by use of N-Bromo- and W-iodosaccharin
Urankar, Damijana,Rutar, Irena,Modec, Barbara,Dolenc, Darko
, p. 2349 - 2353 (2007/10/03)
N-Bromo and N-iodosaccharin react with electron-deficient alkenes such as α,β-unsaturated ketones, acids, esters and nitriles in aqueous organic solvents, yielding the corresponding halohydrins in good yields. The reactions take place at room temperature,
Green approach for the conversion of olefins into vic-halohydrins using N-halosuccinimides in ionic liquids
Yadav,Reddy,Baishya, Gakul,Harshavardhan,Janardhana Chary,Gupta, Manoj Kumar
, p. 3569 - 3572 (2007/10/03)
Alkenes undergo smooth bromo- and iodohydroxylation with N-bromo- and N-iodosuccinimides/water, respectively, using the air and moisture stable ionic liquid [bmim]BF4 as a novel recyclable reaction medium in high to quantitative yields. N-Halosuccinimides show enhanced reactivity in ionic liquids thereby reducing the reaction times and improving the yields considerably.
