6935-75-7Relevant academic research and scientific papers
Rapid assembly of 3-azidomethylfurans from 2-(1-alkynyl)-2-alken-1-ones enabled by silver catalysis
Qian, Lei-Lei,Yi, Ruxia,Min, Xiang-Ting,Hu, Yan-Cheng,Wan, Boshun,Chen, Qing-An
, (2020/06/24)
A rapid access to useful 3-azidomethylfurans is developed via Ag(I)-catalyzed cascade annulation/azidation of 2-(1-alkynyl)-2-alken-1-ones. The salient features of the protocol include mild reaction conditions, high efficiency, broad substrate scope, and
Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Cyclization–[4+3] Annulation Cascades between 2-(1-Alkynyl)-2-alken-1-ones and Anthranils
Chao, Tzu-Hsuan,Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Liu, Rai-Shung
supporting information, p. 10396 - 10400 (2020/04/29)
This work reports gold-catalyzed [4+3]-annulations of 2-(1-alkynyl)-2-alken-1-ones with anthranils to yield epoxybenzoazepine products with excellent exo-diastereoselectivity (dr>25:1). The utility of this new gold catalysis is manifested by applicable substrates over a broad scope. More importantly, the enantioselective versions of these [4+3]-cycloadditions have been developed satisfactorily with chiral gold catalysts under ambient conditions (DCM, 0 °C); the ee levels range from 88.0–99.9 %. With DFT calculations, we postulate a stepwise pathway to rationalize the preferable exo-stereoselection.
Gold(I)-Catalyzed Reactions between 2-(1-Alkynyl)-2-alken-1-ones and Vinyldiazo Ketones for Divergent Synthesis of Nonsymmetric Heteroaryl-Substituted Triarylmethanes: N-versus C-Attack Paths
Kardile, Rahul Dadabhau,Liu, Rai-Shung
supporting information, p. 8229 - 8233 (2020/11/03)
Gold-catalyzed synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes using 2-(1-alkynyl)-2-alken-1-ones and vinyldiazo ketones is described. In this catalytic sequence, vinyldiazo ketones attack gold-containing 3-furylbenzyl cations to form the observed C(1)-addition products. We also note that vinyldiazo ketones can be thermally cyclized to yield pyrazole derivatives, which can react with 3-furylbenzyl cations to afford pyrazole-containing triarylmethanes, corresponding to a N(5)-addition path.
Organocatalytic Formation of Chiral Trisubstituted Allenes and Chiral Furan Derivatives
Poulsen, Pernille H.,Li, Yang,Lauridsen, Vibeke H.,J?rgensen, Danny K. B.,Palazzo, Teresa A.,Meazza, Marta,J?rgensen, Karl Anker
supporting information, p. 10661 - 10665 (2018/07/30)
A novel reaction that provides chiral allenes by amino catalytic activation of either aldehydes or α,β-unsaturated aldehydes for reaction with alkynyl-substituted enones is presented. The reaction forms a variety of trisubstituted allenes in high yields a
Sc(OTf)3-Catalyzed Diastereoselective Formal [3+2] Cycloaddition Reactions of Alkynylcyclopropane Ketones with Electron-Rich Aromatic Aldehydes to Yield 2,5-trans-Tetrahydrofurans
Zhang, Chi,Xu, Muyun,Ren, Jun,Wang, Zhongwen
, p. 2467 - 2478 (2016/06/01)
In contast to the general [4+2] cycloaddition reactions of alkynylcyclopropane ketones reported in the literature, we report herein a Sc(OTf)3-catalyzed formal intermolecular [3+2] cycloaddition reaction of alkynylcyclopropane ketones with elec
Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines
Muzalevskiy, Vasily M.,Ustynyuk, Yury A.,Gloriozov, Igor P.,Chertkov, Vyacheslav A.,Rulev, Alexander Yu.,Kondrashov, Evgeniy V.,Ushakov, Igor A.,Romanov, Alexey R.,Nenajdenko, Valentine G.
, p. 16982 - 16989 (2015/11/16)
The reactions of trifluoromethylated 2-bromoenones and N,N′-dialkyl-1,2-diamines have been studied. Depending on the structures of the starting compounds, the formation of 2-trifluoroacetylpiperazine or 3-trifluoromethylpiperazine-2-ones was observed. The mechanism of the reaction is discussed in terms of multistep processes involving sequential substitution of bromine in the starting α-bromoenones and intramolecular cyclization of the captodative aminoenones as key intermediates to form the target heterocycles. The results of theoretical calculations are in perfect agreement with the experimental data. The unique role of the trifluoromethyl group in this reaction is demonstrated.
Chemoselective C-C bond cleavage of epoxide motifs: Gold(I)-catalyzed diastereoselective [4+3] cycloadditions of 1-(1-Alkynyl)oxiranyl ketones and nitrones
Wang, Tao,Zhang, Junliang
, p. 86 - 90 (2011/03/20)
Cutting carbon! A novel facile strategy for the C-C bond cleavage of oxiranyl ketones has been developed. Carbophilic gold(I) activation of the alkyne side chain mediates a heterocyclization and subsequent C-C bond cleavage (see scheme).
Cascade palladium-catalyzed direct intramolecular arylation/alkene isomerization sequences: Synthesis of indoles and benzofurans
Yagoubi, Myriam,Cruz, Ana C. F.,Nichols, Paula L.,Elliott, Richard L.,Willis, Michael C.
supporting information; experimental part, p. 7958 - 7962 (2011/01/11)
One route, two cycles: A palladium-catalyzed intramolecular direct arylation reaction combined with an isomerization step provided a straightforward synthetic route to both indoles and benzofurans (see scheme). Isolation and functionalization of intermedi
Solvolytic stereoselective debromination of vic-dibromides with HMPA
Khurana,Bansal,Chauhan
, p. 1089 - 1091 (2007/10/03)
A simple and efficient procedure for the debromination of vic-dibromides has been reported with hexamethylphosphoric triamide at 155-160°C under a nitrogen atmosphere without the aid of any reagent.
New Derivatives of N-Vinyltriazoles: 1,3-Diaryl-3-(1H-1,2,4-triazol-1-yl)-2-propen-1-ones
Rekhter, M. A.,Grushetskaya, G. N.,Panasenko, A. A.,Krimer, M. Z.
, p. 792 - 796 (2007/10/03)
We have synthesized previously unknown N-vinyltriazoles: 1,3-diaryl-3-(1H-1,2,4-triazol-1-yl)-2-propen-1-ones.We discusss a hypothesis for a probable reaction mechanism.
