Recent Advances in Alkenyl sp² C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(24), P. 17479 - 17646

Published: Oct. 14, 2022

Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, advanced materials. Significant efforts have been made toward the development new practical methods to access this important class compounds by selectively activating alkenyl C(sp2)–H bonds recent years. In comprehensive review, we describe state-of-the-art strategies for direct functionalization sp2 C–H C–F until June 2022. Moreover, metal-free, photoredox, electrochemical also covered. For clarity, review has divided into two parts; first part focuses on currently available using different alkene as starting materials, second describes bond easily accessible gem-difluoroalkenes material. This includes scope, limitations, mechanistic studies, stereoselective control (using directing groups well metal-migration strategies), applications complex molecule synthesis where appropriate. Overall, aims document considerable advancements, current status, emerging work critically summarizing contributions researchers working fascinating area is expected stimulate novel, innovative, broadly applicable functionalizations coming

Language: Английский

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Recent advances in visible light-mediated chemical transformations of enaminones

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

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Recent advances in the syntheses of pyrroles

Green Synthesis and Catalysis, Journal Year: 2022, Volume and Issue: 4(1), P. 20 - 34

Published: June 23, 2022

The pyrrole moiety is an important structural motif in functional materials, natural products, and pharmaceuticals. More more synthetic strategies toward pyrroles have emerged, where various efficient building blocks are developed these synthons enable the syntheses of with different numbers components. However, no review specifically summarizes according to type number employed blocks. To aid researchers design appropriate substrates for synthesis, herein we summarized advances classified reactions into four categories components, which may shed light on developing methods substituted pyrroles.

Language: Английский

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Electrochemical Organoselenium Catalysis for the Selective Activation of Alkynes: Easy Access to Carbonyl-pyrroles/oxazoles from N-Propargyl Enamines/Amides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3812 - 3817

Published: May 17, 2023

Intramolecular electro-oxidative addition of enamines or amides to nonactivated alkynes was attained access carbonyl-pyrroles -oxazoles from N-propargyl derivatives. Organoselenium employed as the electrocatalyst, which played a crucial role π-Lewis acid and selectively activated alkyne for successful nucleophilic addition. The synthetic strategy permits wide range substrate scope up 93% yield. Several mechanistic experiments, including isolation selenium-incorporated intermediate adduct, enlighten electrocatalytic pathway.

Language: Английский

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Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

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Rh-Catalyzed and Self-Directed Aromatic C–H Activation of Enaminones to Divergent Alkenylated and Annulated Compounds

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

Published: Feb. 27, 2025

By means of simple Rh catalysis, the direct activation ortho-C-H bond in aryl enaminones has been realized with enaminone structure as a traceless directing fragment. The products resulting from C-H alkenylation and further annulation via intramolecular addition could be accessed depending upon alkenes. annulated used for easy synthesis valuable 2-aza-fluorenones one-pot operation by employing NH4OAc.

Language: Английский

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Copper‐Catalyzed Oxidative [1+2+1+2] Cascade Cyclization of N,N‐Dimethyl Enaminones with Benzylamines: A Facile Access to Functionalized 1,4‐Dihydropyridines

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(28)

Published: Feb. 24, 2023

Using benzylamines as the C4 source of 1,4-dihydropyridines (1,4-DHPs), a Cu-catalyzed oxidative [1+2+1+2] cascade cyclization for synthesis 1,4-DHPs was firstly developed. A broad range easily available N,N-dimethyl enaminones and are employed smoothly to provide diverse with high efficiency. This method is performed by one-pot C(sp3 )-H bond functionalization/C(sp3 )-N cleavage/cyclization strategy form simultaneously two )-C(sp2 ) bonds, C(sp2 1,4-DHP ring.

Language: Английский

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Progress in the Study of α-Functionalization of Enaminone

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(2), P. 602 - 602

Published: Jan. 1, 2023

烯胺酮是一类非常重要的有机合成砌块, 具有易获得、储存方便、反应多样性等优点. 更重要的是, 烯胺酮是许 多杂环化合物的重要前体.最近

Language: Английский

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Mechanosynthesis of Pyrrole-2-carboxylic Acids via Copper-Catalyzed Spiroannulation/Ring-Opening Aromatization of 4-Arylidene Isoxazol-5-ones with Enamino Esters

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4189 - 4193

Published: May 14, 2024

An efficient and practical tandem reaction of 4-arylidene isoxazol-5-ones with enamino esters catalyzed by an inexpensive copper salt has been established in a ball mill. This innovative approach yields diverse array structurally novel pyrrole-2-carboxylic acids, showing excellent tolerance toward different functional groups. By integrating spiroannulation ring-opening aromatization processes, this protocol introduces facile cost-effective strategy for synthesizing highly functionalized pyrrole derivatives.

Language: Английский

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Sustainable Synthesis of Indole-Substituted Densely Functionalized Pyrrole

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1407 - 1416

Published: Jan. 10, 2024

A novel chromatography- and catalyst-free methodology has been developed for the synthesis of poly substituted pyrrole in good yields via a multicomponent reaction arylglyoxal, 1,3-dicarbonyl, indole, aromatic amine. This strategy provides various advantages such as simple experimental workup procedures, mild conditions, no added catalyst, use green solvent, purification procedure pure product without using column chromatography. method offers highly effective to synthesize wide range indole–pyrrole conjugates one-pot operation.

Language: Английский

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