Multicomponent Annulative SO₂ Insertion of Heteroatom‐Linked 1,7‐Diynes for Accessing Tricyclic Sulfones

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(10), P. 1693 - 1698

Published: May 6, 2023

Abstract A metal‐free radical multicomponent bicyclization of heteroatom‐linked 1,7‐diynes with aryl diazonium tetrafluoroborates and DABCO‐bis(sulfurdioxide) (DABSO) is reported, enabling annulative SO 2 insertion access to produce two types skeletally diverse tricyclic sulfones, namely, thieno[3,4‐ c ]quinoline 2,2‐dioxides ]chromene 2,2‐dioxides, moderate good yields by simply tuning the linkers 1,7‐diynes. This protocol demonstrates remarkable compatibility regarding N ‐ O ‐linked different substitution patterns tetrafluoroborates. magnified image

Language: Английский

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Visible-Light-Induced Regioselective Cascade Radical Cyclization of α-Bromocarbonyls: Access to Benzazepine Derivatives

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2238 - 2246

Published: Jan. 31, 2024

Visible-light-induced regioselective cascade radical cyclization of α-bromocarbonyls for the synthesis benzazepine derivatives is described. In presence fac-Ir(ppy)3 (2.0 mol %) as a photocatalyst, 2,6-lutidine base, and dichloromethane solvent, reactions proceed smoothly to afford seven-membered rings in good yields. This protocol features broad substrate scope, excellent functional group tolerance, mild reaction conditions. Preliminary mechanistic studies reveal that generation α-carbon more prone react with 1,1-diphenylethylene tethered acrylamide generate stable heterocycle.

Language: Английский

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Lewis/Brønsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(30), P. 4523 - 4526

Published: Jan. 1, 2023

A novel Lewis- and Brønsted-acid mediated electrophilic addition cyclization/amidation reaction of 1,6-enynes with nitriles to synthesize 3-enamide-substituted dihydrobenzofurans has been developed. The transformation involves the a Brønsted acid as reagent enynes, followed by intramolecular cyclization form cationic intermediates, termination nitrile nucleophile. main features include high atom economy chemoselectivity, well construction C-C/C-N bonds in one step.

Language: Английский

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K₂S₂O₈-Mediated Radical Cyclization of 1,6-Enyne for the Synthesis of Diiodonated γ-Lactams

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2393 - 2403

Published: Jan. 30, 2023

A novel and convenient K2S2O8-mediated diiodo cyclization of 1,6-enynes for the facile synthesis functionalized γ-lactam derivatives has been developed. This reaction features mild transition-metal-free conditions, which offer a green efficient entry to synthetically important scaffolds. Mechanistic studies suggest that iodide radicals initiate cascade cyclic transformation.

Language: Английский

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Visible-Light-Driven Photocatalytic Kharasch Reaction of Phenol/ Arylamine-Linked 1,6-Enynes with Perhalogenated Methane

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(12), P. 4282 - 4282

Published: Jan. 1, 2022

Language: Английский

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Electrocatalytic oxidative C–H cycloamination towards tricyclic [1,2,4]triazolo-[3,4-i]purine nucleosides mediated by bromide ions

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5369 - 5374

Published: Jan. 1, 2023

A green and sustainable electrochemical alternative strategy for the synthesis of biologically important [1,2,4]-triazolo-[3,4- i ]-purine derivatives via intramolecular oxidative C–N bond coupling has been established.

Language: Английский

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Radical-Mediated Trifunctionalization Reactions

Molecules, Journal Year: 2024, Volume and Issue: 29(15), P. 3620 - 3620

Published: July 31, 2024

Synthetic radicals have intrinsic power for cascading and multifunctional reactions to construct diverse molecular scaffolds. In the previous review series, we covered 1,2-difunctionalizations, remote 1,3-, 1,4-, 1,5-, 1,6-, 1,7-difunctionalizations, addition followed by cyclization reactions, cycloaddition-initiated difunctionalizations. Presented in this paper are radical addition-initiated trifunctionalization of alkenes, alkynes, their derivatives. After initial addition, there different pathways, such as group or hydrogen atom transfer, cyclization, coupling, complete second third functionalizations.

Language: Английский

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An Introduction to Methanol as a C1 Building Block

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

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Electrochemical Nitro Reduction to Amines Using Pinacolborane as Reducing Agent

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: May 8, 2024

Abstract Nitroaromatic compounds, as hazardous industrial pollutants, have long been extensively studied for their conversion into high-value aromatic amines. However, most of these transformation reactions require either transition-metal catalysts or high-temperature conditions. Therefore, we report an electrochemical approach utilizing pinacolborane the reducing agent efficient reduction nitroaromatic compounds. The reaction is characterized by its mild conditions and simplicity operation, it demonstrates excellent substrate adaptability functional group compatibility.

Language: Английский

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Synthesis of Aminated C-3 Aryloylated Benzofuran, Furopyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne and N-Aminopyridinium Salt in Visible Light

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

We report a visible-light-assisted tandem oxidative 5-

Language: Английский

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