Five-membered ring systems: furans and benzofurans DOI

Halina Kwiecień

Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 251 - 280

Опубликована: Янв. 1, 2023

Язык: Английский

Synthesis of Tetrahydro-indolones through Rh(III)-Catalyzed [3 + 2] Annulation of Enaminones with Iodonium Ylides DOI

Mingshuai Zhang,

Longkun Chen,

Haifeng Sun

и другие.

Organic Letters, Год журнала: 2023, Номер 25(40), С. 7298 - 7303

Опубликована: Окт. 3, 2023

An unprecedented protocol for a Rh(III)-catalyzed [3 + 2] annulation from simple and readily available enaminones iodonium ylides has been developed. The novel strategy allows access to new class of structurally diverse tetrahydro-indolones with high efficiency broad substrate scope. In addition, this transformation represents the first example selective alkenyl C–H bond functionalization enaminones. Finally, potential applications are demonstrated through gram-scale reaction late-stage modification.

Язык: Английский

Процитировано

38

A Comprehensive Review on Benzofuran Synthesis Featuring Innovative and Catalytic Strategies DOI Creative Commons

Aqsa Mushtaq,

Ameer Fawad Zahoor, Sajjad Ahmad

и другие.

ACS Omega, Год журнала: 2024, Номер 9(19), С. 20728 - 20752

Опубликована: Май 6, 2024

Benzofurans have intrigued both pharmaceutical researchers and chemists owing to the medicinal usage of their derivatives against copious disease-causing agents (i.e., bacteria, viruses, tumors). These heterocyclic scaffolds are pervasively encountered in a number natural products drugs. The ever-increasing utilization benzofuran as persuaded devise novel facile methodological approaches assemble biologically potent nucleus. This review summarizes current developments regarding innovative synthetic routes catalytic strategies procure synthesis heterocycles with corresponding mechanistic details, reported by several research groups during 2021-2023.

Язык: Английский

Процитировано

11

The Indenyl Effect: Accelerated C−H Amidation of Arenes via Ind*RhIII Nitrene Transfer Catalysis** DOI Creative Commons
Liselle Atkin, Daniel L. Priebbenow

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(23)

Опубликована: Апрель 6, 2023

Investigations into C-H amidation reactions catalysed by cationic half-sandwich d6 metal complexes revealed that the indenyl-derived catalyst [Ind*RhCl2 ]2 significantly accelerated directed ortho of benzoyl silanes using 1,4,2-dioxazol-5-ones. Ring slippage involving a haptotropic η5 to η3 rearrangement indenyl complex proposedly enables ligand substitution at centre proceed via associative, rather than dissociative pathways, leading significant rate and yield enhancements. Intriguingly, this phenomenon appears specific for weakly coordinating carbonyl-based directing groups with no acceleration observed corresponding strongly nitrogen-based groups.

Язык: Английский

Процитировано

17

Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization DOI

Yicong Ge,

Qiang Yan,

Jiang Nan

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(22), С. 5717 - 5734

Опубликована: Янв. 1, 2023

Vinylene carbonate (VC) has emerged as a promising coupling partner to participate in various attractive C–H conversions and implement an increasing number of novel reactions. In this review, we provide summary the advancements achieved metal-catalyzed functionalization using VC.

Язык: Английский

Процитировано

16

Rhodium‐Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N‐carbamoylindoles with Vinylene Carbonate DOI

Jia‐Lin Song,

Lin Xiao,

Shaoyong Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(9), С. 1457 - 1464

Опубликована: Апрель 14, 2023

Abstract In this study, Rh(III)‐catalyzed C−H bifunctionalization and direct vinylene annulation of sulfoxonium ylides N ‐carbamoylindoles with carbonate was accomplished, which afforded a series naphthalenones containing β‐ketosulfoxonium ylide moiety, isocoumarins, pyrimidones. This protocol featured mild conditions, broad substrate scope, functional‐groups compatibility. addition, related applications preliminary mechanistic exploratory were also investigated magnified image

Язык: Английский

Процитировано

14

Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate DOI

Ayumi Inami,

Yuji Nishii, Koji Hirano

и другие.

Organic Letters, Год журнала: 2023, Номер 25(18), С. 3206 - 3209

Опубликована: Май 4, 2023

Isoquinoline is a privileged structure in many bioactive compounds and valuable ligands. Transition-metal-catalyzed oxidative annulation of imine derivatives has become promising synthetic method; however, catalytic synthesis 3,4-nonsubstituted isoquinolines by formal acetylene been scarce to date. Herein, we introduce vinyl selenone as an effective surrogate for the Rh-catalyzed annulative coupling under mild conditions. The Se fragment can be recovered diselenide recycled. product readily converted 1-aminoisoquinolines.

Язык: Английский

Процитировано

11

Chemical upcycling of poly(bisphenol A carbonate) to vinylene carbonates through organocatalysis DOI Creative Commons
Killian Onida,

Mohamad Fayad,

Sébastien Norsic

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(11), С. 4282 - 4291

Опубликована: Янв. 1, 2023

The chemical upcycling of poly(bisphenol A carbonate) was carried out through organocatalysis using α-hydroxyketones as nucleophiles, leading to valuable vinylene carbonates.

Язык: Английский

Процитировано

11

Vinylene Carbonate as Synthon in Transition Metal‐Catalyzed C−H Bond Activation/Annulation Reactions DOI Open Access

Xiaofan Cui,

Rémi Chauvin, Chao Pi

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(20), С. 3400 - 3412

Опубликована: Сен. 6, 2023

Abstract Recently, vinylene carbonate has been developed as a powerful synthon in transition metal‐catalyzed C−H bond activation/cyclization reactions. This review introduces recent progress the use of reactant, by analyzing and comparing reaction models involving surrogate ethynol, acetylene, acetylation reagents or other reactants, while addressing related mechanisms synthetic applications.

Язык: Английский

Процитировано

11

Rhenium-catalyzed synthetic method of 1,2-dihydroisoquinolines and isoquinolines by the intramolecular cyclization of 2-alkynylaldimines or 2-alkynylbenzylamines DOI

Rui Umeda,

Tetsuya Ishida,

Shintaro Mori

и другие.

Tetrahedron, Год журнала: 2024, Номер 154, С. 133854 - 133854

Опубликована: Фев. 2, 2024

Язык: Английский

Процитировано

4

Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate DOI
Jiang Nan, Qiong Huang,

Xinran Men

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(26), С. 3571 - 3574

Опубликована: Янв. 1, 2024

Herein, a novel Pd-catalyzed denitrogenation/vinylation of benzotriazinones using vinylene carbonate as the vinylation reagent is reported. This transformation demonstrates an unprecedented skeletal editing approach, effectively converting NN to CC fragments

Язык: Английский

Процитировано

4