Catalytic asymmetric silicon-carbon bond-forming transformations based on Si-H functionalization

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(6), P. 1654 - 1687

Published: May 4, 2023

Language: Английский

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Theoretical study of an N-heterocyclic carbene-catalyzed annulation reaction between an enal and a β-silyl enone: Mechanism and origin of stereoselectivity

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 551, P. 113621 - 113621

Published: Oct. 27, 2023

Language: Английский

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Copper-Catalyzed Markovnikov Selective 3,4-Hydrosilylation of 2-Substituted 1,3-Dienes

Organic Letters, Journal Year: 2022, Volume and Issue: 24(22), P. 4081 - 4086

Published: June 1, 2022

A copper-catalyzed regioselective Markovnikov 3,4-hydrosilylation of 2-substituted 1,3-dienes has been accomplished. wide range and trihydrosilanes are compatible under the optimal conditions. The bisphosphine ligand with a rigid backbone provides product in better yield selectivity. Besides, synthetic utilities allylsilanes also were demonstrated by their flexible derivatizations.

Language: Английский

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Copper-catalyzed three-component annulation toward pyrroles via the cleavage of two C–C bonds in 1,3-dicarbonyls

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(71), P. 10636 - 10639

Published: Jan. 1, 2023

The first copper-catalyzed three-component annulation of α,β-unsaturated ketoximes, 1,3-dicarbonyls and paraformaldehyde has been documented. This novel strategy achieved the two C-C bond cleavage 1,3-dicarbonyl compounds directly as a single-carbon synthon provided new highly efficient method for synthesis 2,3-disubstituted pyrroles in moderate to good yields with broad functional group compatibility.

Language: Английский

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Synthesis of chiral systems featuring the pyrrole unit: a review

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Synthetic strategies towards pyrroles within chiral frameworks are summarised, focussing on reports published 2010–2023.

Language: Английский

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Copper-catalyzed formal [4 + 1] annulation ofN-propargyl ynamides with diketones

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(1), P. 203 - 208

Published: Nov. 24, 2022

An efficient copper-catalyzed formal [4 + 1] annulation of N -propargyl ynamides with diketones has been developed, allowing practical and atom-economic synthesis valuable pyrrole-substituted dioxoles in generally moderate to excellent yields.

Language: Английский

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Construction of Spirolactams by Unexpected Oxidative Cyclization of Alkenyl Diynes via Copper Catalysis

Organic Letters, Journal Year: 2023, Volume and Issue: 25(9), P. 1525 - 1529

Published: March 1, 2023

A copper-catalyzed oxidative cyclization of alkenyl N-propargyl ynamides is described. This protocol enables the practical synthesis diverse spirocyclic γ-lactams bearing an exocyclic double bond with generally high Z/E selectivity in moderate to good yields. Importantly, this demonstrates a distinctive comparison related gold catalysis.

Language: Английский

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Copper-catalyzed intermolecular formal (5 + 1) annulation of 1,5-diynes with 1,2,5-oxadiazoles

Communications Chemistry, Journal Year: 2023, Volume and Issue: 6(1)

Published: Sept. 12, 2023

Abstract One-carbon homologation reactions based on one-carbon insertion into the N−O bond of heterocycles have received tremendous interest over past decades. However, these protocols to rely use hazardous and not easily accessible diazo compounds as precursors, examples relevant asymmetric catalysis been reported. Here we show that a copper-catalyzed intermolecular formal (5 + 1) annulation 1,5-diynes with 1,2,5-oxadiazoles involving heterocyclic via non-diazo approach. This method enables practical atom-economic synthesis valuable pyrrole-substituted oxadiazines in generally moderate good yields under mild reaction conditions. In addition, possibility such an also emerges.

Language: Английский

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Synthesis of a new fluorophore: wavelength-tunable bisbenzo[f]isoindolylidenes

Chemical Science, Journal Year: 2023, Volume and Issue: 14(45), P. 13151 - 13158

Published: Jan. 1, 2023

The creation of new functional molecules is a central task in chemical synthesis. Herein, we report the synthesis type fluorophore, bisbenzo[f]isoindolylidenes, from easily accessible dipropargyl benzenesulfonamides. Wavelength-tunable fluorophores emitting strong fluorescence green to red light were obtained this reaction. Late-stage modifications and incorporation bioactive into these give rise potential applications biological studies. Detailed computational experimental studies conducted elucidate mechanism, suggest reaction sequence involving Garratt-Braverman cyclization, isomerization, fragmentation, dimerization oxidation.

Language: Английский

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Direct synthesis of α-functionalized amides via heteroatom–hydrogen insertion reactions using amide-sulfoxonium ylides

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Nov. 25, 2024

α-Functionalized Si-, Ge-, B-, Se-, and S-amide moieties are present in many medicinally active molecules, but their synthesis remains challenging. Here, we demonstrate a high-throughput using amide-sulfoxonium ylides as carbene precursors Si-H, Ge-H, B-H, Se-H, S-H insertion reactions to target wide range of α-silyl, α-geryl, α-boryl, α-selenyl, α-sulfur (hetero)amides. The process is featured simple operation, mild conditions, broad substrate scope, high functional group compatibility, excellent chemoselectivity. Both experimental computational studies conducted explore the mechanisms underlying formation C-Si/Ge/B/Se/S bond. This research highlights use highly selective X-H with ylide-derived carbenes, paving way for preparation diverse organosilane, organogermane, organoboron, organoselenium, organosulfur compounds from accessible bench-stable precursors.

Language: Английский

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