2425-29-8Relevant academic research and scientific papers
Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes
Iakovenko, Roman,Hlavá?, Jan
supporting information, p. 440 - 446 (2021/01/28)
Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is
Cooperative Lewis acid-onium salt catalysis as tool for the desymmetrization of meso-epoxides
Broghammer, Florian,Brodbeck, Daniel,Junge, Thorsten,Peters, René
, p. 1156 - 1159 (2017/01/25)
Epoxide desymmetrizations by bromide are very rare despite the large synthetic potential of chiral bromohydrins. Herein we present a new concept for epoxide desymmetrizations in which a bifunctional Lewis acid/ammonium salt catalyst allows for efficient enantio-selective epoxide ring openings by Br. With acetylbromide as a Br source bromohydrin esters are formed.
Polystyrene bound dioxidovanadium(V) complexes of 2-acetylpyridine derived ligands for catalytic oxidations
Maurya, Mannar R.,Chaudhary, Nikita,Kumar, Amit,Avecilla, Fernando,Costa Pessoa, Jo?o
, p. 24 - 38 (2014/07/08)
Three neat complexes [VVO2(acpy-bhz)] (1) [V VO2(acpy-inh)] (2) and [VVO2(acpy- nah] (3) and the corresponding polymer-supported (PS) dioxidovanadium(V) complexes having monobasic tridentat
Polymer and non-polymer-grafted dioxidomolybdenum(VI) complexes having ONO donor ligand and their catalytic activities for the oxidative bromination of organic substrates
Maurya, Mannar R.,Kumar, Naveen,Avecilla, Fernando
, p. 50 - 60 (2014/06/10)
The ligand H2sal-iah (I), derived from salicylaldehyde and indole-3-acetic hydrazide, reacts with [MoVIO2(acac) 2] in methanol to give dioxidomolybdenum(VI) complex [Mo VIO2(sal-iah)(MeOH)]
Polymer-grafted and neat vanadium(V) complexes as functional mimics of haloperoxidases
Maurya, Mannar R.,Chaudhary, Nikita,Avecilla, Fernando
, p. 436 - 448 (2013/11/19)
The monobasic tridentate ONN donor ligand 1-(2-pyridylazo)-2-naphthol [Hpan (I)] reacts with [VIVO(acac)2] in dry methanol to yield the oxidovanadium(IV) complex [VIVO(acac)(pan)] (1). The dioxidovanadium(V) complex [{VVO(pan)}2(μ-O) 2] (2) is obtained by aerial oxidation of 1 in methanol. Complex 2 can also be prepared directly by reacting [VIVO(acac)2] with I followed by aerial oxidation in methanol. Treatment of 1 or 2 in methanol with H2O2 yields the oxidomonoperoxidovanadium(V) complex [VVO(O2)(pan)(MeOH)] (3). Reaction of imidazolomethylpolystyrene cross-linked with 5% divinylbenzene (PS-im) with 2 in DMF resulted in the formation of the polymer-grafted dioxidovanadium(V) complex PS-im[VVO2(pan)] (4). All these complexes are characterized by various spectroscopic techniques (IR, electronic, NMR ( 1H and 51V) and electron paramagnetic resonance (EPR)), thermal, field-emission scanning electron micrographs (FE-SEM) as well as energy dispersive X-ray (EDX) studies. The crystal and molecular structure of 3 has been determined, confirming the ONN binding mode of I. The polymer-grafted complex 4 has been used for the oxidative bromination of styrene, salicylaldehyde and trans-stilbene. Various parameters, such as amounts of catalyst, oxidant (aqueous 30% H2O2), KBr and aqueous 70% HClO4 have been optimized to obtain the maximum oxidative bromination of the substrates. Under the optimized reaction conditions, styrene gave a maximum of 99% conversion after 2 h of reaction, with the main products having a selectivity order of: 1-phenylethane-1,2-diol (75%) > 2-bromo-1- phenylethane-1-ol (20%) > 1,2-dibromo-1-phenylethane (1.2%). With nearly same conversion in same time, the oxidative bromination of salicylaldehyde gave three products with the selectivity order: 5-bromosalicylaldehyde > 2,4,6-tribromophenol > 3,5-dibromosalicylaldehyde. A maximum of 91% conversion of trans-stilbene has been obtained in 2 h of reaction time, where selectivity of the obtained reaction products varied in the order: 2,3-diphenyloxirane (trans-stilbene oxide) > 1,2-dibromo-1,2-diphenylethane > 2-bromo-1,2-diphenylethanol. The catalytic activity of the non-polymer grafted complex 2 is lower than that of the polymer-grafted one. In addition, the recycling ability of the grafted complex makes it better over the neat complex.
CF3CO2ZnEt-mediated highly regioselective rearrangement of bromohydrins to aldehydes
Wang, Zhihui,Li, Meiyi,Zhang, Wenqin,Jia, Jiangnan,Wang, Fei,Xue, Song
supporting information; experimental part, p. 5968 - 5971 (2011/11/29)
A highly efficient and selective rearrangement reaction of bromohydrins to aldehydes mediated by CF3CO2ZnEt was described. The secondary and tertiary aldehydes were prepared under mild conditions in good to excellent yields (85-99%). The scope and limitations of this rearrangement process were also investigated.
Allyltin tribromide: A versatile reagent involved in the ring-opening of epoxides
Chen, Guohong,Wang, Xin,Jin, Xiaoqian,Liu, Lingyan,Chang, Weixing,Li, Jing
experimental part, p. 1294 - 1301 (2010/11/05)
This paper presents a versatile reagent for epoxide cleavage. The allyltin tribromide could act as a novel and easily prepared allylation reagent and halide atom donor to convert epoxides to the corresponding homoallyl alcohols and halohydrins in high yields with excellent regioselectivities under mild reaction conditions, respectively. It could also act as a Lewis acid to catalyze the ring opening reactions of epoxides with alcohols.
Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent
Patil, Rajendra D.,Joshi, Girdhar,Adimurthy, Subbarayappa,Ranu, Brindaban C.
experimental part, p. 2529 - 2532 (2009/09/06)
A new method for the preparation of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent has been developed. Several α-bromoketones were successfully prepared from a variety of olefins by this method. This procedure is an alternative to conventional molecular bromine.
An efficient vanadium-catalyzed bromination reaction
Moriuchi, Toshiyuki,Yamaguchi, Mitsuaki,Kikushima, Kotaro,Hirao, Toshikazu
, p. 2667 - 2670 (2008/02/03)
An efficient catalytic oxidative bromination of arenes, alkenes, and alkynes in aqueous media was achieved under relatively mild conditions by using NH4VO3 catalyst combined with H2O2, HBr, and KBr. Dodecyltrimethylammonium bromide was found to serve as an efficient surfactant to facilitate the NH4VO3-catalyzed bromination in aqueous media.
Chemoselective conversion of aromatic epoxide and 1,2-diol to 1,3-dioxane derivatives with phenyltrimethylammonium tribromide in the presence of a catalytic amount of antimony(III) bromide
Sayama, Shinsei
, p. 4001 - 4005 (2007/10/03)
trans-Stilbene oxide was oxidatively converted to 2-phenyl-1,3-dioxanes with phenyltrimethylammonium tribromide in the presence of various 1,3-diols and a catalytic amount of SbBr3 in DMSO at room temperature. Aromatic 1,2-diol, such as hydrobenzoin, was similarly converted to 2-aryl-1,3-dioxane derivatives under the same reaction conditions.
