16619-57-1Relevant academic research and scientific papers
Dichlorination of olefins with diphenyl sulfoxide/oxalyl chloride
Ding, Rui,Huang, Shuai,Wang, Qiyi,Liu, Yongguo,Sun, Baoguo,Tian, Hongyu
supporting information, p. 2319 - 2330 (2020/07/03)
The combination of diphenyl sulfoxide and oxalyl chloride was used to accomplish the dichlorination of olefins, in which chlorodiphenylsulfonium salt generated in situ was proposed to be the real active species as a chloronium ion source.
Synthesis method of Z-type halogenated chalcone compound
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Paragraph 0034; 0036; 0037, (2018/12/13)
The invention relates to a synthesis method of a Z-type halogenated chalcone compound as shown in formula (III), characterized by comprising: by using a compound shown in formula (I) and a compound shown in formula (II) as reaction raw materials, using IPrAuCl as a catalyst, using AgSbF as an assistant and using 1,2-dichloroethane as a solvent, performing a reaction at the room temperature; andafter ending the reaction, carrying out post treatment on reaction liquid to obtain the Z-type halogenated chalcone compound as shown in formula (III). The synthesis method disclosed by the inventionis simple and short in step, mild in condition, very high in reaction speed, meanwhile, high in yield and good in regioselectivity, and is a green and economic reaction process; (The formulas are shown in the description.).
E - Z isomerization in Suzuki cross-couplings of haloenones: Ligand effects and evidence for a separate catalytic cycle
Chehal, Navneet K.,Budzelaar, Peter H. M.,Hultin, Philip G.
, p. 1134 - 1143 (2018/02/22)
Suzuki cross-coupling of haloalkenes is generally assumed to occur with retention of the alkene stereochemistry. While studying Suzuki cross-couplings on E-1,2-dichlorovinyl phenyl ketone, we were surprised to observe extensive isomerization. More surprisingly, the ligand employed strongly influenced the degree of isomerization: DPEphos and Xantphos led to 96% isomerized cross-coupled product whereas reactions in the absence of a phosphine ligand, or reactions employing t-BuXantphos, gave 94% retention of stereochemistry. While E-Z isomerization in Pd-catalyzed vinylic couplings has previously been attributed to events within the cross-coupling catalytic cycle, we present experimental and computational evidence for a separate Pd-catalyzed isomerization process in these reactions.
Desulfurative Chlorination of Alkyl Phenyl Sulfides
Canestrari, Daniele,Lancianesi, Stefano,Badiola, Eider,Strinna, Chiara,Ibrahim, Hasim,Adamo, Mauro F. A.
, p. 918 - 921 (2017/02/26)
The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ4-sulfurane intermediate is proposed.
Vanadium(V)-mediated rearrangement/halogenation cascade: Synthesis of α-haloenones from propargyl alcohols
Zhao, Meng,Mohr, Justin T.
, p. 4115 - 4124 (2017/06/29)
A method is described for the oxidative Meyer–Schuster-type rearrangement of propargylic alcohols to (Z)-α-chloro- and α-iodoenones using VOCl3 as a multifunctional reagent. The vanadium reagent is found to serve as rearrangement promoter as well as an active chlorenium ion donor. Yields are improved when VOCl3 is employed in conjunction with N-halosuccinimide reagents, giving some insights into the complex mechanism.
Nucleophilic substitution of α-haloenones with phenols
Mareev, Alexander V.,Ushakov, Igor A.,Rulev, Alexander Yu.
, p. 1971 - 1974 (2015/03/30)
The α-haloenones undergo cine-substitution upon reaction with phenolic reagents under basic conditions. A convenient method for the synthesis of push-pull aroxyenones was developed based on this reaction.
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.
An approach to synthesis of (Z)-2-chloro-1,3-diarylpropen-1-ones by Vilsmeier reagent (bis-(trichloromethyl) carbonate/DMF)
Weng, Yi Yi,Li, Jian Jun,Su, Wei Ke
experimental part, p. 1395 - 1398 (2012/06/01)
A series of (Z)-2-chloro-1,3-diarylpropen-l-ones were unexpectedly synthesized in moderate yields by treatment of easily available 2,3-epoxy-l, 3-diarylpropan-1-ones with Vilsmeier reagent, which was derived from bis(trichloromethyl) carbonate (BTC, triph
Preparation of (Z)-α-chloro-α,β-unsaturated ketones with total or high diastereoselectivity
Concellón, José M,Huerta, Mónica
, p. 7775 - 7780 (2007/10/03)
(Z)-α-Chloroenones are obtained by reaction of α-chloro-β-hydroxyketones with acetic anhydride, pyridine and 4-dimethylaminopyridine with total or high diastereoselectivity and in high yield.
