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

Chemical Reviews, Год журнала: 2022, Номер 122(24), С. 17479 - 17646

Опубликована: Окт. 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

Язык: Английский

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Base-Promoted Regioselective Annulation of Pyridinium Ylides and Bromoalkynes for the Chemodivergent Synthesis of Indolizines

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 5, 2025

A base-promoted regioselective formal [3 + 2] annulation of pyridinium ylides with bromoalkynes is reported, producing a series substituent-diverse indolizines in generally good yields. mild K2CO3-promoted three-component cyclization and at 2:1 molar ratio delivered C2-acylmethylated indolizines, whereas C2-brominated were generated starting from bearing strong electron-withdrawing groups the unit by using 2,2,6,6-tetramethyl-1-piperidinyloxy as dehydrogenating reagent. The current synthetic methodology offers controllable modular approach to access different substitution patterns, featuring wide substrate scope, functional group compatibility, complete regioselectivity without demand any transition-metal catalysts.

Язык: Английский

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Palladium-Catalyzed Cascade Carbonylation Reaction: Synthesis of Fused Isoindolinones

Organic Letters, Год журнала: 2024, Номер 26(27), С. 5625 - 5629

Опубликована: Июль 2, 2024

A palladium-catalyzed cascade carbonylation reaction of 2-bromo-

Язык: Английский

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Pyridinium Ylide-Mediated Diastereoselective Synthesis of Spirocyclopropanyl-pyrazolones via Cascade Michael/Substitution Reaction

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 8230 - 8242

Опубликована: Май 14, 2024

We have devised a highly diastereoselective formal [2 + 1] annulation reaction of arylidene/alkylidine-pyrazolones with in situ-generated supported as well standard pyridinium ylides to construct spirocyclopropanyl-pyrazolones. The cascade approach exhibits wide range functional group tolerance, gram-scale capability, and substrate versatility. A diverse spirocyclic cyclopropanes was synthesized extensively both mediators, the pyridine reused subsequent cycles. Density theory calculations confirmed formation spirocyclopropane lower energy pathway.

Язык: Английский

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Base-controlled selective cleavage of the C–F bond of difluorocarbene for the divergent assembly of indolizines

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4214 - 4218

Опубликована: Янв. 1, 2024

A [3 + 1 1] cascade annulation reaction for the divergent construction of trisubstituted indolizines using sulfoxonium ylides, BrCF 2 CO Me and pyridinium salts as readily available substrates has been developed.

Язык: Английский

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Visible-Light-Mediated α-Ketoacylations of NH-Sulfoximines with gem-Difluoroalkenes

Organic Letters, Год журнала: 2022, Номер 24(3), С. 907 - 911

Опубликована: Янв. 18, 2022

A photochemical approach for the preparation of α-keto-N-acyl sulfoximines from NH and gem-difluoroalkenes has been developed. In presence NBS, reactions proceed in air without need a photocatalyst or additional oxidant. Results mechanistic studies suggest that two oxygens products stem water dioxygen.

Язык: Английский

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Copper‐Catalyzed [3+2] Annulation of Pyridinium Ylides with α‐CF₃ Ketones: Synthesis of Functionalized 2‐Fluoroindolizines

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Март 23, 2023

Abstract A copper‐catalyzed [3+2] annulation of the in situ generated pyridinium ylides with α‐CF 3 ketones was realized, which first acted as synthetic equivalents unstable fluoroalkynones. With this protocol, a series functionalized 2‐fluoroindolizines were afforded moderate to good yields under ambient conditions air oxidant.

Язык: Английский

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Controllable stepwise fluorine elimination strategy for the chemodivergent synthesis of pyrido[2,1-a]isoquinolines

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Март 1, 2025

Язык: Английский

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Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 19, 2025

A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- oxidant-free [3 + 2] cycloaddition reaction zwitterionic ketenimines pyridinium salts. This versatile method proceeds under mild conditions, affording in moderate to good yields. approach involves an intermolecular cycloaddition, followed by enamine/imine tautomerization aromatization. Notably, this demonstrates broad functional group compatibility allows facile scalability, making it valuable tool indolizine-based frameworks organic medicinal chemistry.

Язык: Английский

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Progress in N-α-C(sp³)—H Bond Functionalization for the Synthesis of N-Heterocycles

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(4), С. 1047 - 1047

Опубликована: Янв. 1, 2025

Язык: Английский

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