Regioselective tandem sulfonylation/cyclization of unsaturated N-substituted enamides with sulfonyl chlorides by copper catalysis

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5784 - 5790

Опубликована: Янв. 1, 2024

The radical cascade cyclization of vinyl-tethered alkenes has become a promising tool for rapidly assembling nonbenzene-fused cyclic skeletons via the cracking alkenyl C–H bonds, but this approach been limited to generate five-membered rings.

Язык: Английский

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Easy Access to Phenanthrenes Through Photoinduced Difunctionalization of Alkynes

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 686 - 686

Опубликована: Янв. 1, 2025

Язык: Английский

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Alkoxycarbonylation-triggered nitrile insertion/remote C(sp²)–H and C(sp³)–H functionalization to access esterified quinazolinones and amidines

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 3861 - 3867

Опубликована: Янв. 1, 2024

A new alkoxycarbonyl radical triggered nitrile insertion/remote C(sp 2 )–H and 3 functionalization reaction is developed.

Язык: Английский

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Acid-catalyzed radical tandem alkylation/cyclization of unactivated alkenes with ketones: Access to ketoalkyl-substituted quinazolinone derivatives

Tetrahedron, Год журнала: 2024, Номер 162, С. 134085 - 134085

Опубликована: Июнь 11, 2024

Язык: Английский

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Near-Infrared-Light-Induced Iron(I) Dimer-Enabled Radical Cascade Reactions of Fluoroalkyl Bromides for the Synthesis of Ring-Fused Quinazolinones

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7976 - 7980

Опубликована: Сен. 6, 2024

The use of an earth-abundant and inexpensive iron complex as a catalyst, coupled with near-infrared (NIR) light the energy source, for radical reactions alkyl halides has been far less developed. In this study, we report NIR light-mediated iron(I) dimer-catalyzed cascade fluoroalkyl bromides synthesis ring-fused quinazolinones bearing difluoromethyl group. process, 3-bromo-1,10-phenanthroline ligand facilitates reactivity [CpFe(CO)

Язык: Английский

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Photoredox/HAT-Catalyzed Intramolecular Hydrocyclization of Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 2, 2024

New photochemical approaches to 2,3-fused quinazolinones and dihydroquinazolinones are disclosed. The intramolecular hydrocyclization proceeds in moderate excellent yields across diverse alkenes with high regioselectivity diastereocontrol. Mechanistic studies indicated that the radical cascade processes involve thiophenol acting as single-electron transfer hydrogen atom reagents. success of gram-scale synthesis proves strategy can be used for practical applications.

Язык: Английский

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Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 18, 2024

We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range unactivated alkenes, using inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) produce diverse array heterocycles containing sulfonyl thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- transition-metal-free, broad scope substrates. Preliminary mechanistic studies suggest reaction involves combination electrolysis reductive quenching photocatalytic cycle TPPT.

Язык: Английский

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Photoredox-catalyzed intramolecular oxy- and aminoacylation of alkenes with acyl oxime esters: facile synthesis of acylated saturated heterocycles

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(1), С. 74 - 82

Опубликована: Ноя. 17, 2023

In the present paper, an efficient photoredox-catalyzed intramolecular oxy- and aminoacylation of internal alkenes equipped with pendant oxygen- or nitrogen-centered nucleophiles acyl oxime esters is reported. Under visible-light irradiation, a variety structurally diverse acylated saturated heterocycles, such as tetrahydrofurans, tetrahydropyrans, δ-valerolactones, tetrahydropyrroles, piperidines, tetrahydro-1,3-oxazepines, etc., were efficiently synthesized from easily accessible unsaturated alcohols, carboxylic acids, tosyl-protected amines, O-homoallyl benzimidates via radical-mediated cascade acylation/cyclization process. This light-driven transformation features broad substrate scope, good functional group compatibility, high regio- diastereoselectivity, mild reaction conditions, representing general practical procedure toward construction heterocycles well their derivatives.

Язык: Английский

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Ag/Au-Catalyzed Functionalization of Heterocycles Through C–H Activation

Topics in heterocyclic chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Язык: Английский

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Sulfonyl Radical-Induced Regioselective Cyclization of Enamide–Olefin To Form Sulfonylated 6–7-Membered Cyclic Enamines

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15733 - 15738

Опубликована: Окт. 16, 2024

Remarkable progress has been made in the radical cascade cyclization of heteroaryl- or aryl-tethered alkenes to construct benzene-fused frameworks via cracking aryl C–H bonds. In contrast, linear dienes through vinyl bonds nonbenzene-fused ring with endocyclic double significantly lagged behind, and major advances have largely restricted generation 5-membered heterocycles, such as pyrrolinones. Herein, we report silver-mediated regioselective sulfonylation-cyclization sodium sulfinates form sulfonylated 6- 7-membered cyclic enamines.

Язык: Английский

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