90399-66-9Relevant academic research and scientific papers
Oxidation of α,β-Unsaturated Ketones by Organophotocatalysis Using Rhodamine 6G under Visible Light Irradiation: Insight into the Reaction Mechanism
Yoshioka, Eito,Takahashi, Hiroki,Wanibe, Hikari,Hontani, Yukina,Hatsuse, Kouki,Shimizu, Remi,Kawashima, Akira,Kohtani, Shigeru,Miyabe, Hideto
, p. 697 - 704 (2021/11/13)
The oxidative transformation of α,β-unsaturated ketones was investigated under visible-light-induced photocatalytic conditions using rhodamine 6G as an organophotocatalyst. In this organocatalysis, the mild co-oxidant bromotrichloromethane (BrCCl3) acts n
Catalytic asymmetric intra- and intermolecular haloetherification of enones: An efficient approach to (?)-Centrolobine
Zhou, Pengfei,Cai, Yunfei,Zhong, Xia,Luo, Weiwei,Kang, Tengfei,Li, Jun,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
, p. 7778 - 7783 (2018/05/23)
A catalytic asymmetric intra- and intermolecular haloetherification of electron-deficient alkenes (halogen = Cl, Br, I) has been realized by the use of chiral metal complexes of N,N′-dioxides. In the presence of a chiral Fe(III) complex, a series of tetrahydropyran derivatives were obtained in good yields (up to 99% yield) with a high level of enantioselectivities (up to 97% ee). Promoted by a chiral Ce(III) complex, chiral oxepane derivatives could be given in good results. Moreover, the intermolecular haloetherification of chalcones catalyzed by Sc(III) complex using MeOH as nucleophile is demonstrated. This methodology also can be successfully applied to the synthesis of (?)-Centrolobine. Meanwhile, a reasonable reaction mechanism was proposed.
Alkoxybromination of olefins using ammonium bromide and oxone
Kumar, Macharla Arun,Naresh, Mameda,Rohitha, Chozhiyath Nappunni,Narender, Nama
supporting information, p. 3121 - 3129 (2014/01/06)
A mild, efficient, and highly regio- and stereoselective method for the methoxy and ethoxy bromination of olefins has been developed using NH 4Br as a bromine source and Oxone as an oxidant. Various kinds of olefins (aromatic, linear, and cyclic olefins) afforded the corresponding alkoxy brominated products in moderate to excellent yields. Taylor & Francis Group, LLC.
[Cu(dap)2Cl] as an efficient visible-light-driven photoredox catalyst in carbon-carbon bond-forming reactions
Pirtsch, Michael,Paria, Suva,Matsuno, Taisuke,Isobe, Hiroyuki,Reiser, Oliver
supporting information; experimental part, p. 7336 - 7340 (2012/09/08)
Copper sees the light of day: [Cu(dap)2Cl] proved to be an excellent photoredox catalyst for atom-transfer radical addition reactions, as well as for allylation reactions (see scheme), providing an attractive alternative to commonly used iridium- and ruthenium-based catalysts. Copyright
A regioselective and stereoselective methoxy bromination of olefins using diacetoxyiodobenzene and phenyltrimethyl ammoniumtribromide
Hangirgekar,Shirodkar
experimental part, p. 179 - 184 (2012/01/13)
A facile regio and stereoselective methoxy-bromination of alkenes using phenyltrimethyl ammoniumtribromide (PTAB) and (diacetoxyiodo) benzene (DIB) as oxidant has been carried out in the present investigation. The IR, NMR and LCMS of all the synthesized compounds have been used to characterize them.
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.
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.
Action of tetrabutylammonium tribromide with para-substituted chalcones in protic and aprotic media
Berthelot, Jacques,Benammar,Yamina,Desmazieres, Bernard
, p. 1526 - 1530 (2007/10/03)
Bromination of the double bond of para-substituted chalcones under mild conditions in aprotic solvents is accomplished with high yields using tetrabutylammonium tribromide (TBABr3).In methanol, the main reaction is (α-β) bromoethoxylation.Stereoselectivity, regioselectivity, and chemioselectivity of this bromomethoxylation reaction are described.Key words: bromination, bromoethoxylation, tetrabutylammonium tribromide, (α-β) dibromodihydrochalcones, α-bromo-β-methoxydihydrochalcones.
