Insights into the Activation Mode of α‐Carbonyl Sulfoxonium Ylides in Rhodium‐Catalyzed C−H Activation: A Theoretical Study
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DOI: 10.1002/open.202100254
Abstract: Abstract A computational study has been performed to investigate the mechanism of RhIII‐catalyzed C−H bond activation using sulfoxonium ylides as a carbene precursor. The stepwise and concerted activation modes for sulfoxonium ylides were investigated. Detailed… read more here.
Keywords: activation; insights activation; sulfoxonium ylides; activation mode ... See more keywords
Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas
Sign Up to like & getrecommendations! Published in 2021 at "Chinese Chemical Letters"
DOI: 10.1016/j.cclet.2021.02.052
Abstract: Abstract Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient… read more here.
Keywords: sulfoxonium ylides; synthesis aminothiazoles; carbenoid insertion; rhodium ... See more keywords
A novel synthesis of diversely functionalized 1,2,4-triones through the homo- and cross-coupling reactions of β-keto sulfoxonium ylides
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DOI: 10.1016/j.tetlet.2020.151912
Abstract: Abstract A novel synthesis of functionalized 1,2,4-triones via an oxidative homo-coupling of β-keto sulfoxonium ylides is presented. Preliminary mechanistic study reveals that the formation of the 1,2,4-trione product involves the in situ generation of an… read more here.
Keywords: sulfoxonium ylides; keto sulfoxonium; novel synthesis; functionalized triones ... See more keywords
Annulation of CF3-Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles.
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DOI: 10.1021/acs.orglett.1c02598
Abstract: A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, and the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have been obtained in 27-78% yield. This reaction features a broad substrate scope and… read more here.
Keywords: trisubstituted trifluoromethylpyrroles; cf3 imidoyl; imidoyl sulfoxonium; dicarbonyl compounds ... See more keywords
Iridium(III)-Catalyzed B(4)-Acylmethylation and B(3,5)-Diacylmethylation from o-Carboranes and Sulfoxonium Ylides.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00103
Abstract: An iridium(III)-catalyzed regioselective acylmethylation of the cage B(4)-H bond in o-carborane acids with sulfoxonium ylides is demonstrated through B(4)-H activation in ethanol under very mild conditions, affording a number of B(4)-acylmethylated o-carboranes. Additionally, the selective… read more here.
Keywords: iridium iii; catalyzed acylmethylation; sulfoxonium ylides; acylmethylation ... See more keywords
Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures
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DOI: 10.1021/acs.orglett.2c02204
Abstract: The 1,1a,2,7b-tetrahydrocyclopropa[c]chromene, arising from fusion of chromane and cyclopropane rings is the core of medicinally relevant compounds. Engaging sulfoxonium ylides in enantioselective aminocatalytic reactions for the first time, a convenient entry to this scaffold is… read more here.
Keywords: enantioselective entry; cyclopropane; ylides aminocatalysis; aminocatalysis enantioselective ... See more keywords
Visible-Light-Promoted Synthesis of 1,3-Dicarbonyl Sulfoxonium Ylides.
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DOI: 10.1021/acs.orglett.2c02346
Abstract: A novel visible-light-promoted coupling of diazoketones with sulfoxonium ylides, employing a violet light-emitting diode, is described under both batch and continuous flow conditions. This transformation permits the direct synthesis of synthetically useful 1,3-dicarbonyl sulfoxonium ylides… read more here.
Keywords: sulfoxonium; light promoted; synthesis; dicarbonyl sulfoxonium ... See more keywords
Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α-Carbonyl Sulfoxonium Ylides
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DOI: 10.1021/acs.orglett.2c03396
Abstract: Enantioselective cyclopropanation of α-carbonyl sulfoxonium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular cyclopropanation of SY in the presence of a chiral diene… read more here.
Keywords: cyclopropanation carbonyl; iridium; carbonyl sulfoxonium; cyclopropanation ... See more keywords
Hydroxyl-Directed Ru(II)-Catalyzed Synthesis of Fused Dihydrofurans Using 1,4-Dioxane and Sulfoxonium Ylides as Annulating Agents.
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DOI: 10.1021/acs.orglett.2c04068
Abstract: An unprecedented annulation reaction is developed for the synthesis of dihydrofuran-fused compounds. In this Ru-catalyzed hydroxyl-group-directed reaction, easily affordable sulfoxonium ylides and 1,4-dioxane were used as the annulating partners. This is the first example of… read more here.
Keywords: directed catalyzed; dioxane; synthesis; hydroxyl directed ... See more keywords
Visible-Light-Mediated Photoredox Carbon Radical Formation from Aqueous Sulfoxonium Ylides.
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DOI: 10.1021/acs.orglett.3c00143
Abstract: The visible-light-induced photoredox carbon radical formation from aqueous sulfoxonium ylides has been demonstrated for the first time. While direct reduction of sulfoxonium ylides by H2O efficiently generates the corresponding hydrocarbon compounds, the use of additional… read more here.
Keywords: formation aqueous; sulfoxonium; aqueous sulfoxonium; carbon radical ... See more keywords
Cascade C-H Activation/Annulation of Sulfoxonium Ylides with Vinyl Cyclopropanes: Access to Cyclopropane-Fused α-Tetralones.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c00650
Abstract: Rh-catalyzed weak and traceless directing-group-assisted cascade C-H activation and annulation of sulfoxonium ylides with vinyl cyclopropanes as a coupling partner have been accomplished to furnish functionalized cyclopropane-fused tetralones at moderate temperature. The C-C bond formation,… read more here.
Keywords: annulation sulfoxonium; vinyl cyclopropanes; cascade activation; ylides vinyl ... See more keywords