- Palladium-Catalyzed Amination/Dearomatization Reaction of Indoles and Benzofurans
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This report describes a palladium-catalyzed dearomatization and amination tandem reaction of 2,3-disubstituted indoles and benzofurans via the Catellani strategy. This reaction provides a new method for the construction of amino-substituted indoline-fused cyclic and benzofuran spiro compounds in good yields. The reaction has broad functional group compatibility and substrate scope.
- Zhang, Zhe,Zhang, Bo-Sheng,Li, Kai-Li,An, Yang,Liu, Ce,Gou, Xue-Ya,Liang, Yong-Min
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p. 7817 - 7839
(2020/07/16)
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- Palladium-Catalyzed Dearomative Allylic Alkylation of Indoles with Alkynes to Synthesize Indolenines with C3-Quarternary Centers
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A palladium-catalyzed dearomative allylic alkylation of indoles with alkynes to construct indolenines with C3-quarternary centers was reported. The in situ formed arylallene intermediate omitted the need to install leaving groups on the allylic compounds and employ extra oxidants to oxidize the allylic C-H bonds. The reaction exhibited good functional group tolerance and high atom economy. Moreover, the reaction was further expanded to synthesize pyrroloindolines and furanoindolines.
- Gao, Shang,Wu, Zijun,Fang, Xinxin,Lin, Aijun,Yao, Hequan
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supporting information
p. 3906 - 3909
(2016/08/16)
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- Novel and Efficient Heterogeneous 4-Methylbenzenesulfonic Acid-Based Ionic Liquid Supported on Silica Gel for Greener Fischer Indole Synthesis
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In this work, a functionalizing active species 4-methylbenzenesulfonic acid-based IL on silica gel (IL-SO3H-SiO2) has been prepared, and characterized by FT-IR, XRD, TGA, SEM and EDX spectra. Then, IL-SO3H-SiO2 was utilized as an efficient and heterogeneous catalyst for the synthesis of indoles via the one-pot Fischer reaction of phenyl hydrazines with ketones or aldehydes at room temperature. The heterogeneous catalyst could be recovered easily by filtration and reused many times without significant loss of its catalytic activity.
- Hu, Yu-Lin,Fang, Dong,Li, Dong-Sheng
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p. 968 - 976
(2016/04/20)
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- Iridium- and ruthenium-catalysed synthesis of 2,3-disubstituted indoles from anilines and vicinal diols
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A straightforward and atom-economical method is described for the synthesis of 2,3-disubstituted indoles. Anilines and 1,2-diols are condensed under neat conditions with catalytic amounts of either [Cp*IrCl2] 2/MsOH or RuCl3·xH2O/phosphine (phosphine = PPh3 or xantphos). The reaction does not require any stoichiometric additives and only produces water and dihydrogen as byproducts. Anilines containing methyl, methoxy, chloro and fluoro substituents can participate in the cyclocondensation. Meta-substituted anilines give good regioselectivity for 6-substituted indoles, while unsymmetrical diols afford excellent regioselectivity for the indole isomer with an aryl or large alkyl group in the 2-position. The mechanism for the cyclocondensation presumably involves initial formation of the α-hydroxyketone from the diol. The ketone subsequently reacts with aniline to generate the α-hydroxyimine which rearranges to the corresponding α-aminoketone. Acid- or metal-catalysed electrophilic ring-closure with the release of water then furnishes the indole product.
- Tursky, Matyas,Lorentz-Petersen, Linda L. R.,Olsen, Lasse B.,Madsen, Robert
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experimental part
p. 5576 - 5582
(2011/02/18)
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