22965-96-4Relevant academic research and scientific papers
Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process
Du, Chan,Fang, Jianghua,Fang, Yewen,Lei, Wan,Li, Yan,Liu, Yongjun
supporting information, p. 8502 - 8506 (2021/10/20)
Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.
Formation of substituted 2-iminooxazolidines via intermolecular 1,2-addition/intramolecular N-vinylation using 3-substituted-2-bromo-2-propen-1-ols as substrates
Weischedel, Heike,Schmidt, Dietmar,Conrad, Jürgen,Beifuss, Uwe
, p. 6426 - 6441 (2018/09/27)
The Cu2O-catalyzed reaction between equimolar amounts of easily available 3-substituted-2-bromo-2-propen-1-ols and dicyclohexyl carbodiimide in DMSO at 100 °C using K3PO4 as the base and in the absence of any additive excl
Photo-induced tandem cyclization of 3-iodoflavones with electron rich five-membered heteroarenes
Yang, Qian,Wang, Rui,Han, Jie,Li, Chenchen,Wang, Tao,Liang, Yong,Zhang, Zunting
, p. 43206 - 43211 (2017/09/15)
Vinyl radicals were generated from 3-iodoflavones under a mercury lamp and tandem cyclization reactions occurred with five-membered heteroarenes entailing two consecutive C-C bond formations to synthesize benzo[e]chromeno[2,3-g]indol-13(1H)-one derivatives. The tandem cyclization reactions worked in acetonitrile without any additives such as transition metals, ligands and oxidants, giving rise to a broad variety of novel polycyclic xanthone frameworks in good yield under mild and environmentally friendly reaction conditions.
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.
Hydride transfer versus electron transfer in the reduction of 4-phenyl-3-halo-3-buten-2-ones mediated by Pichia stipitis
Zampieri, Davila S.,Zampieri, Luiz A.,Rodrigues, J. Augusto R.,De Paula, Bruno R.S.,Moran, Paulo J.S.
experimental part, p. 289 - 293 (2012/07/03)
Reductions of (Z)-C6H5CHCXC(O)CH3 (X = Cl, Br) mediated by Pichia stipitis gave 4-phenylbutan-2-one through dehalogenation of intermediaries 3-halo-4-phenylbutan-2-one by an electron transfer mechanism. The addition of 1,3-dinitrobenzene avoids the dehalogenation and thus the corresponding (2S,3S)-halohydrins were obtained in excellent enantiomeric excesses by a hydride transfer mechanism. Irganox 1010 and 1076 were also used to inhibit the electron transfer mechanism. The obtained halohydrins are important chiral building blocks to obtain optically active epoxides and aminoalcohols.
Trifluoromethylation of alkenyl bromides and iodides (including 5-iodouracils) with (CF3)2Hg and Cu (" trifluoromethylcopper")
Nowak, Ireneusz,Robins, Morris J.
, p. 2678 - 2681 (2007/10/03)
Bromo- and iodoalkenes undergo trifluoromethylation efficiently in DMA with "CF3Cu" generated from (CF3)2Hg and Cu. Variable stereochemical inversion is observed with substrates having a gem-carbonyl group. Substrates having gem-hydrogen, -alkyl, or -alkenyl groups give products with stereochemical retention.
The α-arylation of α-bromo- and α-chloroenones using palladium-catalysed cross-coupling
Banks, James C.,Mele, David Van,Frost, Christopher G.
, p. 2863 - 2866 (2007/10/03)
The palladium-catalysed cross-coupling reaction of various arylboronic acids with α-bromoenones and α-chloroenones offers an operationally simple approach to the synthesis of both cyclic and acyclic α-arylenones.
A convenient halogenation of α,β-unsaturated carbonyl compounds with OXONE and hydrohalic acid (HBr,HCl)
Kim, Kyoung-Mahn,Park, In-Hwan
, p. 2641 - 2644 (2007/10/03)
Mixtures of OXONE and hydrobromic acid or hydrochloric acid afford solutions of bromine or chlorine, respectively, α-Bromo- or α-chloro-α,β-unsaturated carbonyl compounds were prepared by addition of hydrobromic acid or hydrochloric acid to the mixture of
Versatile Transformations of α,β-Dibromoesters and Ketones in Basic Media under Microwave Irradiation
Hamelin, Jack,Saoudi, Aicha,Benhaoua, Hadj
, p. 2185 - 2188 (2007/10/03)
Depending on the reaction medium, α,β-dibromoesters under microwave irradiation may selectively lead to α-bromoalk-enes, to alkenes or to (E)-β-bromostyrenes. The corresponding ketones give selectively the α-bromoketones.
α-hypervalent iodine functionalized phosphonium and arsonium ylides and their tandem reaction as umpolung reagents
Huang, Zhizhen,Yu, Xiaochun,Huang, Xian
, p. 8261 - 8264 (2007/10/03)
α-Hypervalent iodine functionalized phosphonium and arsonium ylides 2 can be used as umpolung ylides to react with nucleophiles to give α-heteroatom substituted ylides 4 in good yields. The nucleophilic substitution - Wittig tandem reaction of 2 can occur smoothly to provide an efficient method for the synthesis of (Z)-α-halo-α,β-unsaturated enoates or enones 6, stereoselectively.
