Visible-Light-Induced Cascade Cyclization of 3-(2-(Ethynyl)phenyl)quinazolinones to Phosphorylated Quinolino[2,1-b]quinazolinones

Organic Letters, Journal Year: 2022, Volume and Issue: 24(43), P. 7912 - 7917

Published: Oct. 21, 2022

3-(2-(Ethynyl)phenyl)quinazolinones were designed and synthesized as a class of novel efficient skeletons for phosphorylation/cyclization reactions. Under visible light irradiation, series phosphorylated quinolino[2,1-b]quinazolinones (35 examples, up to 87% yield) first from 3-(2-(ethynyl)phenyl)quinazolinones diarylphosphine oxides by using 4CzIPN photocatalyst under mild conditions. This reaction was also applicable sunlight irradiation. Moreover, the efficiency could be significantly improved continuous-flow

Language: Английский

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Divergent Construction of Thiochromanes and N-Arylbutanamides via Arylthiodifluoromethyl Radical-Triggered Cascade of Alkenes

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13279 - 13290

Published: Aug. 31, 2023

A strategy utilizing silver-catalyzed oxidative decarboxylation radical cascade cyclization of arylthiodifluoroacetic acids with alkenes for the simple and efficient preparation difluoromethylated thiochromanes 2,2-disubstituted-N-arylbutanamides derivatives has been developed. This approach includes good functional group tolerance, easily accessible starting materials, operational simplicity.

Language: Английский

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Pd-catalyzed imine-directed one-pot access to polysubstituted pyrrolesviatandem triple isocyanide insertion/aza-Nazarov cyclization reactions

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(13), P. 3252 - 3258

Published: Jan. 1, 2023

A novel one-pot method for synthesizing polysubstituted pyrrole derivatives via three-component reactions of alkenyl bromides, amines, and isocyanides is reported by Pd catalysis, without additional ligands, with the orderly insertion three isocyanide molecules.

Language: Английский

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Divergent Conversion of Double Isocyanides with Alkenyl Bromide to Polysubstituted Pyrroles and 4-Imino-4,5-dihydropyrrolo[3,4-b]pyrrol-6(1H)-one Derivatives by Pd-Catalyzed Tandem Cyclization Reactions

Organic Letters, Journal Year: 2022, Volume and Issue: 24(3), P. 859 - 863

Published: Jan. 12, 2022

Herein a novel and concise approach to pyrrole skeletons via Pd-catalyzed tandem cyclization reactions is investigated. The substrates for the transformation could be readily prepared by phosphoric acid-catalyzed Ugi with available starting materials. In this strategy, two isocyanides participate in sequential isocyanide insertion reactions, chemoselectivity of products regulated steric hindrance isocyanide. A plausible mechanism formation corresponding adducts proposed.

Language: Английский

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Base-Dependent Divergent Carbodifluoroalkylation and Halodifluoroalkylation of Alkenes under Visible-Light Irradiation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13457 - 13471

Published: Sept. 3, 2024

Organic molecules containing a difluoroalkyl group are valuable and versatile chemicals because of their unique physicochemical biological properties. Accordingly, the development efficient practical difluoroalkylation for preparation these compounds is important attractive. Herein, we demonstrate photoredox-catalyzed base-dependent selective carbodifluoroalkylation halodifluoroalkylation alkenes using readily available 2-(allyloxy)arylaldehydes [or 2-(allylamino)arylaldehydes] XCF

Language: Английский

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Photoinduced radical cyclization reaction of isocyanides with α-carbonyl bromides to access 11-alkyl-substituted 1,4-dibenzodiazepines

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A photochemical radical cascade cyclization reaction of isocyanides with α-carbonyl bromides under mild conditions is disclosed for accessing 1,4-dibenzodiazepines, demonstrating good tolerance towards various functional groups.

Language: Английский

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Mn(III) Catalyzed Cascade Cross-coupling / Annulation / C(O)-C Bond Insertion / Rearrangement: Access to Multi-substituted Indolenines in Water

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

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N-Aryl/-Alkenyl difluoroketenimines: transient intermediates for the general synthesis of difluoroalkylated heterocycles

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

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Mn(III)-Mediated Radical Addition/Cyclization of Isocyanides with Aryl Boronic Acids/Diarylphosphine Oxides: Access to 11-Functionalized Dibenzodiazepines

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(1), P. 198 - 210

Published: Dec. 22, 2022

A Mn(III)-mediated radical addition/cyclization reaction of isocyanides with aryl boronic acids/diarylphosphine oxides has been developed. series 11-arylated/-phosphorylated dibenzodiazepines were efficiently constructed in moderate to excellent yields under mild conditions via imidoyl process. The present protocol offers novel access functionalized seven-membered N-heterocycles.

Language: Английский

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Photoinduced Cascade C–N/C═O Bond Formation from Bromodifluoroalkyl Reagents, Amines, and H₂O via a Triple-Cleavage Process

Organic Letters, Journal Year: 2022, Volume and Issue: 24(8), P. 1668 - 1672

Published: Feb. 22, 2022

A green, sustainable, and straightforward method for the synthesis of unsymmetrical oxalamides via photoinduced C–N/C═O bond formation bromodifluoroacetamide, amine, H2O through a triple-cleavage process has been developed. In addition, this approach also provides access to known bioactive compounds, feasible reaction mechanism is proposed. Moreover, advantages transformation, including mild conditions, broad substrate scope, operational simplicity, make protocol attractive further applications.

Language: Английский

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