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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Multiple-fold C–F bond functionalization for the synthesis of (hetero)cyclic compounds: fluorine as a detachable chemical handle

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(7), С. 2013 - 2055

Опубликована: Янв. 1, 2022

We highlighted the recent advances in field of multiple-fold C–F bond functionalization for synthesis (hetero)cyclic compounds.

Язык: Английский

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Coupling partner-dependent unsymmetrical C–H functionalization of N-phenoxyacetamides leading to sophisticated spirocyclic scaffolds

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(17), С. 4583 - 4590

Опубликована: Янв. 1, 2022

In this paper, a coupling partner-dependent unsymmetrical C–H functionalization of N -phenoxyacetamides leading to the formation sophisticated spirocyclic scaffolds is presented.

Язык: Английский

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Synthesis of fluorine-containing bicyclo[4.1.1]octenes via photocatalyzed defluorinative (4+3) annulation of bicyclo[1.1.0]butanes with gem-difluoroalkenes

Chemical Science, Год журнала: 2024, Номер unknown

Опубликована: Дек. 13, 2024

This manuscript presents a photoredox-catalyzed defluorinative (4 + 3) annulation of bicyclo[1.1.0]butanes with gem -difluoroalkenes, providing practical and straightforward access to the fluorine-containing bicyclo[4.1.1]octenes.

Язык: Английский

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Construction of Benzoxazole and Isoquinoline Compounds via Base-Mediated Cyclization of Amino Acid Derivatives

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 19, 2025

Biological organisms contain bioactive macromolecules such as amino acids, which serve basic materials for constructing cells and repairing tissues. Due to the unique properties of fluorine atom, can alter structure proteins increase their lipophilicity, incorporating a atom into acids has become research hotspot. In this study, ethyl 3-bromo-2-((diphenylmethylene)amino)-3,3-difluoropropanoate was synthesized from glycine derivatives. Under alkaline conditions, compound reacted with 2-aminophenol generate benzoxazole-containing acid derivative. This method is simple operate, without metal participation, performed under relatively eco-friendly reaction providing novel approach synthesis benzoxazole heterocycles.

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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Synthesis of gem-difluorinated pentacyclic indenopyrazolopyrazolones via Rh(iii)-catalyzed cascade C–H functionalization/[3 + 2] dipolar cycloaddition

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2512 - 2517

Опубликована: Янв. 1, 2024

A Rh( iii )-catalysed cascade C–H functionalization/[3 + 2] dipolar cycloaddition was realized to deliver gem -difluorinated pentacyclic indenopyrazolopyrazolones with four continuous chiral carbon centres in a one-pot fashion.

Язык: Английский

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DABCO‐Promoted Selective Photochemical C−N Coupling: Access to Unsymmetrical Azahelicenes

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(21), С. 3690 - 3703

Опубликована: Сен. 16, 2023

Abstract A multifaceted study on the effect of various factors efficiency photocyclization naphthofuran O‐acyl oximes was performed. It showed that without any additives or in presence electron acceptors, reaction occurs by a radical pathway and with low chemoselectivity, while DABCO promotes intramolecular cyclization to give naphthofuroquinolines (NFQs) 34–87% yields. The iminyl formed under UV irradiation due single transfer (SET) N−O bond cleavage undergoes selective homolytic aromatic substitution (HAS) formation new C−N bond. This route quinoline‐annulated scaffolds is based use both as an agent proton acceptor.

Язык: Английский

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Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes

Science China Chemistry, Год журнала: 2023, Номер 66(10), С. 2842 - 2846

Опубликована: Июнь 6, 2023

Язык: Английский

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Practical conversion of gem-difluorocyclopropenes for the chemodivergent assembly of fluorinated heterocyclic frameworks

Green Chemistry, Год журнала: 2023, Номер 25(24), С. 10630 - 10637

Опубликована: Янв. 1, 2023

A green method has been established by employing gem -difluorocyclopropylenes as versatile building blocks, leading to the chemodivergent formation of several fluorinated structural motifs including cyclopropapyrazolopyridines, indolizines etc .

Язык: Английский

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