Five-membered ring systems: furans and benzofurans DOI

Halina Kwiecień

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 251 - 280

Published: Jan. 1, 2023

Language: Английский

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

Mingshuai Zhang,

Longkun Chen,

Haifeng Sun

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(40), P. 7298 - 7303

Published: Oct. 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.

Language: Английский

Citations

38
A Comprehensive Review on Benzofuran Synthesis Featuring Innovative and Catalytic Strategies DOI Creative Commons

Aqsa Mushtaq,

Ameer Fawad Zahoor, Sajjad Ahmad

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(19), P. 20728 - 20752

Published: May 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.

Language: Английский

Citations

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, Journal Year: 2023, Volume and Issue: 62(23)

Published: April 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.

Language: Английский

Citations

17
Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization DOI

Yicong Ge,

Qiang Yan,

Jiang Nan

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5717 - 5734

Published: Jan. 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.

Language: Английский

Citations

16
Rhodium‐Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N‐carbamoylindoles with Vinylene Carbonate DOI

Jia‐Lin Song,

Lin Xiao,

Shaoyong Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1457 - 1464

Published: April 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

Language: Английский

Citations

14
Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate DOI

Ayumi Inami,

Yuji Nishii, Koji Hirano

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(18), P. 3206 - 3209

Published: May 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.

Language: Английский

Citations

11
Chemical upcycling of poly(bisphenol A carbonate) to vinylene carbonates through organocatalysis DOI Creative Commons
Killian Onida,

Mohamad Fayad,

Sébastien Norsic

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(11), P. 4282 - 4291

Published: Jan. 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.

Language: Английский

Citations

11
Vinylene Carbonate as Synthon in Transition Metal‐Catalyzed C−H Bond Activation/Annulation Reactions DOI Open Access

Xiaofan Cui,

Rémi Chauvin, Chao Pi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3400 - 3412

Published: Sept. 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.

Language: Английский

Citations

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

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 154, P. 133854 - 133854

Published: Feb. 2, 2024

Language: Английский

Citations

4
Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate DOI
Jiang Nan, Qiong Huang,

Xinran Men

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(26), P. 3571 - 3574

Published: Jan. 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

Language: Английский

Citations

4