Copper-Catalyzed Annulation of O-Acyl Oximes with Cyclic 1,3-Diones for the Synthesis of 7,8-Dihydroindolizin-5(6H)-ones and Cyclohexanone-Fused Furans

Organic Letters, Journal Year: 2023, Volume and Issue: 25(5), P. 838 - 842

Published: Jan. 27, 2023

A copper-catalyzed annulation of O-acyl oximes with cyclic 1,3-diones has been developed for the concise synthesis 7,8-dihydroindolizin-5(6H)-ones and cyclohexanone-fused furans through substituent-controlled selective radical coupling process. 2-Alkyl undergo C-C coupling, while 2-unsubstituted C-O coupling.

Language: Английский

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Nitrogen heterocycle construction in aqueous mediums: A sustainable tool for molecular diversity

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2023, Volume and Issue: 40, P. 100756 - 100756

Published: Jan. 14, 2023

Language: Английский

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Dialkylation of 1,3-Dienes with Aldehydes and Cyclopropanols toward Homoallylic Alcohols by Dual Photoredox and Chromium Catalysis

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 27, 2025

A visible-light-induced three-component coupling of aldehydes, 1,3-dienes, and cyclopropyl alcohols using dual photoredox chromium catalysis is herein described. This efficient protocol achieves the dialkylation 1,3-dienes toward 1,4-disubstituted homoallylic in moderate to good yields with excellent regioselectivity, featuring mild reaction conditions, functional group tolerance, gram-scale synthesis. Mechanistic study suggests that photoinduced sequential ring opening alcohol radical nucleophilic cascade addition are involved catalytic cycle.

Language: Английский

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Copper-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4229 - 4234

Published: May 13, 2024

A copper-catalyzed [3 + 2] annulation of

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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Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(10), P. 109565 - 109565

Published: Feb. 1, 2024

Language: Английский

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Metal-free three-component tandem cyclization for modular synthesis of 2,3-dihydrobenzothiazin-4-ones

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2021 - 2026

Published: Jan. 1, 2024

The first three-component cyclization reaction of benzo[ c ][1,2]dithiol-3-ones based on S–S bond cleavage is disclosed herein.

Language: Английский

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Copper-catalyzed [3+2] annulation of O-acyl ketoximes with 2-aryl malonates for the synthesis of 3-aryl-4-pyrrolin-2-ones

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(35), P. 5225 - 5228

Published: Jan. 1, 2023

A copper-catalyzed [3+2] annulation of O -acyl ketoximes with 2-aryl malonates for the concise synthesis 3-aryl-4-pyrrolin-2-ones has been developed.

Language: Английский

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An HFIP-assisted, cobalt-catalyzed three-component electrophilic C–H amination/cyclization/directing group removal cascade to naphtho[1,2-d]imidazoles

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(37), P. 5595 - 5598

Published: Jan. 1, 2023

A concise and efficient method has been developed herein for the synthesis of valuable naphtho[1,2-d]imidazole derivatives. It involves an earth-abundant cobalt-catalyzed electrophilic ortho C-H amination/cyclization/directing group removal cascade with O-benzoloxyamines using paraformaldehyde as a one carbon synthon. Picolinamide utilized traceless directing group. boosting effect HFIP is found in whole process. The reaction conditions are very simple allow easy handling, making this methodology appealing.

Language: Английский

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Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13076 - 13088

Published: Aug. 31, 2023

An unexpected copper-mediated radical-induced ring-opening relay cascade carboannulation reaction of [60]fullerene with cyclobutanone oxime esters is presented for the preparation various Cl-/Br-incorporated [60]fullerene-fused cyclopentanes. The unique transformation uses inexpensive copper salts as promoters and halogen sources features simple redox-neutral conditions a broad substrate scope, providing practical access to class novel five-membered carbocycle-fused fullerenes.

Language: Английский

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