Visible-Light-Induced Decarboxylative Annulation of α,β-Unsaturated Acids with Amines and α-Keto Acids for 2,4-Diarylquinoline Synthesis

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 3, 2025

An efficient and sustainable approach for the synthesis of 2,4-diarylquinolines has been developed via a visible-light-promoted metal-free three-component decarboxylative annulation pathway. This one-pot protocol combines readily available feed-stock α,β-unsaturated acids, aromatic amines, α-keto acids in cascade manner to access substituted quinolines under eco-benign conditions. Moreover, mechanistic insights suggest initial C-C cross coupling followed by 6π electrocyclic afford desired products. The broad substrates scope excellent functional group tolerance make this more attractive synthetically applicable toward construction complex N-heterocycles.

Язык: Английский

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External Reductant-Free Palladium-Catalyzed Reductive Insertion of Isocyanide: Synthesis of Polysubstituted Pyrroles and Its Applications as a Cysteine Probe

Organic Letters, Год журнала: 2019, Номер 21(11), С. 4044 - 4048

Опубликована: Май 10, 2019

In this work, an unprecedented route is described for the synthesis of 2-amino-4-cyanopyrrole derivatives via palladium-catalyzed reductive isocyanide insertion alkynyl imines. reactions, no external reductant added and plays a dual role as both C1 synthon imidoylation cyano source cyanation. Mechanism studies suggest [4 + 1] cycloaddition, insertion, β-carbon elimination, palladium hydride-based reduction are involved. Moreover, application 2-amine-4-cyanopyrroles cysteine probe realized to detect cysteine.

Язык: Английский

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Recent Advances in Palladium-Catalyzed Isocyanide Insertions

Molecules, Год журнала: 2020, Номер 25(21), С. 4906 - 4906

Опубликована: Окт. 23, 2020

Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function a CO-substitute palladium-catalyzed cross couplings. Over the past decades, isocyanides emerged practical and C1 building blocks, whose inherent N-substitution for rapid incorporation of nitrogeneous fragments wide variety products. Recent developments palladium catalyzed isocyanide insertion reactions significantly expanded scope applicability these imidoylative cross-couplings. This review highlights advances made this field over eight years.

Язык: Английский

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Divergent oriented synthesis (DOS) of aza-heterocyclic amides through palladium-catalyzed ketenimination of 2-iodo-N-(propa-1,2-dien-1-yl)anilines

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(6), С. 890 - 895

Опубликована: Янв. 1, 2020

A palladium-catalyzed tandem reaction of N-(2-iodophenyl)-4-methyl-N-(propa-1,2-dien-1-yl)benzenesulfonamide with isocyanide is described to divergently produce aza-heterocyclic amides.

Язык: Английский

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Enhanced Activity of MOF-Based Pd/Electron-Transfer Mediator Catalysts in Oxidation Reactions Involving Isonitrile by Defect Engineering

ACS Catalysis, Год журнала: 2024, Номер 14(16), С. 12064 - 12073

Опубликована: Июль 29, 2024

Herein, we report a Pd/electron-transfer mediator (ETM) catalyst "Pd/Cu-UiO-67(N)x" based on defect-engineered metal–organic frameworks (MOFs), which exhibits high activity and stability in the aminoamidation reaction of N-sulfonyl-2-allyl aniline with isonitrile insertion. The Pd turnover number Pd/Cu-UiO-67(N)x system is about 30 times higher than that existing catalytic systems by decreasing loading base. This work systematically investigates specific effects defects activation reactants. rationally anchored Pd(II) Cu(II) framework interact O2 trapped defective MOF to achieve reoxidation Pd(0). strategy not only confers species but also provides access application MOFs large-size substrate transformations.

Язык: Английский

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Oxygen-, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect

Organic Process Research & Development, Год журнала: 2024, Номер 28(8), С. 2988 - 3025

Опубликована: Июль 13, 2024

Язык: Английский

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TMSOTf-Catalyzed [4 + 2] Annulation of Ynamides and β-(2-Aminophenyl)-α,β-ynones for the Synthesis 2-Aminoquinolines

Organic Letters, Год журнала: 2024, Номер 26(17), С. 3503 - 3508

Опубликована: Апрель 25, 2024

A metal-free TMSOTf-catalyzed [4 + 2] annulation of ynamides with β-(2-aminophenyl)-α,β-ynones enables the regiospecific and facile assembly 2-aminoquinoline frameworks. The catalyst TMSOTf presented a remarkable advancement compared to previously reported transition-metal catalysts. wide range 3-aryl/alkyl-substituted 2-aminoquinolines were generated in moderate excellent yields due mild conditions.

Язык: Английский

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Direct Assembly of Polysubstituted Propiolamidinates via Palladium-Catalyzed Multicomponent Reaction of Isocyanides

Organic Letters, Год журнала: 2019, Номер 21(20), С. 8439 - 8443

Опубликована: Окт. 9, 2019

A straightforward approach for the assembly of different polysubstituted propiolamidnates via palladium-catalyzed multicomponent reaction isocyanides, haloalkynes, and amines has been reported in which C(sp)–C(sp2) C(sp2)═N bonds were constructed one pot. This featured high efficiency, excellent chemoselectivity, good functional group compatibility. The synthetic utility this method was also demonstrated.

Язык: Английский

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Palladium-Catalyzed Cycloaddition of Alkynylimines, Double Isocyanides, and H₂O/KOAc

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(10), С. 6441 - 6449

Опубликована: Апрель 23, 2020

In this work, a palladium-catalyzed cyclization of alkynylimines and double isocyanides is described. This facile procedure efficient for synthesizing various 4-amidyl-2-aminopyrroles. Mechanism investigation indicates that four-membered ring-fused pyrrole species key intermediate the reaction involves [4 + 1] cycloaddition, protonation, nucleophilic addition, 1,4-addition isocyanide, rearomatization. Interestingly, linear dipyrrole derivative found to be an appropriate fluoride ion probe with remarkable emission change, which could serve as potential candidate optoelectronic conjugated materials.

Язык: Английский

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MOF-based Pd catalysts: a controllable and efficient platform towards cyclization reactions of isonitriles

Green Chemistry, Год журнала: 2022, Номер 24(23), С. 9203 - 9210

Опубликована: Янв. 1, 2022

The state transformation of Pd( ii ) x -UiO-67-bpy, which is illustrated by “homogenization heterogeneous catalysis”, endows the system with efficiency and eco-friendliness.

Язык: Английский

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