Site-Selective Copper–N-Heterocyclic Carbene-Catalyzed C(sp2)–C(sp) Cross-Coupling of Aryl Thianthrenium Salts DOI
Jin Zhang, Hangsheng Yang, Li Sun

et al.

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

Published: March 23, 2025

This work demonstrates Cu–NHC (NHC = N-heterocyclic carbene) catalyzed alkynylation of aryl thianthrenium salts via thiazol-2-ylidene ligands, achieving a Pd-free Sonogashira coupling with broad substrate compatibility and functional group tolerance. Late-stage pharmaceutical rare alkynylative C–H functionalization/ring-opening pathways are enabled. Thiazol-2-ylidenes, featuring "half-umbrella"-shaped geometry, exhibit superior catalytic performance over traditional imidazol-2-ylidenes, underscoring their unique ligand efficacy. catalysis enables the use as versatile electrophiles for diverse cross-couplings under mild conditions.

Language: Английский

Sulfoxonium ylides: simple compounds with chameleonic reactivity DOI
Giorgiana Denisa Bisag, Silvia Ruggieri, Mariafrancesca Fochi

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(43), P. 8793 - 8809

Published: Jan. 1, 2020

Sulfur ylides first disclosed in 1930 started to gain more attention the 1960s, thanks mainly studies by Corey and Chaykovsky on their use for preparation of strained rings. More recently, chemistry these compounds has experienced important growth, part due similarity reactivities with diazo compounds. This short review provides an overview great assortment reactions sulfoxonium ylides, outlining a comparison between congeners: sulfonium Insertion reactions, cyclisation ring-opening are highlighted, giving particular catalytic asymmetric methodologies.

Language: Английский

Citations

117
Recent advances in Rh(iii)/Ir(iii)-catalyzed C–H functionalization/annulation via carbene migratory insertion DOI
Sanjeev Kumar, Saiprasad Nunewar,

Srilekha Oluguttula

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(7), P. 1438 - 1458

Published: Jan. 1, 2021

The review highlighted diverse annulations, including nitrogen, oxygen, sulfur heterocycles and carbocylizations via Rh(iii)/Ir(iii)-catalyzed C–H functionalization/annulation with various arene carbene precursors.

Language: Английский

Citations

91
C–H functionalization of quinazolinones by transition metal catalysis DOI
Prasanjit Ghosh, Bhaskar Ganguly, Sajal Das

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(24), P. 4497 - 4518

Published: Jan. 1, 2020

Quinazolinone and its congeners are ubiquitous structural motifs found in numerous natural products due to their wide applications as anticancer, antiviral, anti-inflammatory, antifolate antitumor agents etc. Previously, the synthetic community devoted efforts towards approaches but recent years have also witnessed an upsurge diversification of this scaffold applications. Thus, review (from 2011 beginning 2020) comprehensively focuses on transition metal catalyzed C-H bond functionalization namely arylation, amination, acetoxylation, amidation, alkylation, alkenylation, alkynylation, halogenation, thiolation, trifluoroethylation quinazolin-4(3H)-one. Additionally, we briefly elucidate plausible mechanistic pathways, scope limitations.

Language: Английский

Citations

76
Application of sulfoxonium ylide in transition-metal-catalyzed C-H bond activation and functionalization reactions DOI
Anil Kumar, Mahadev Sharanappa Sherikar, Vinayak Hanchate

et al.

Tetrahedron, Journal Year: 2021, Volume and Issue: 101, P. 132478 - 132478

Published: Oct. 8, 2021

Language: Английский

Citations

71
Co(III), Rh(III) & Ir(III)‐Catalyzed Direct C−H Alkylation/Alkenylation/Arylation with Carbene Precursors DOI
Saiprasad Nunewar, Sanjeev Kumar,

Srilakshmi Talakola

et al.

Chemistry - An Asian Journal, Journal Year: 2021, Volume and Issue: 16(5), P. 443 - 459

Published: Jan. 15, 2021

Metal carbenes play a pivotal role in transition-metal-catalyzed synthetic transfer reactions. The metal carbene is generated either from diazo compound through facile extrusion of N2 with catalyst or situ other sources like triazoles, pyriodotriazoles, sulfoxonium ylides and iodonium-ylide. On the hand, Co(III), Rh(III) & Ir(III)-catalyzed C-H functionalizations have been well established as key step to enable construction various transformations. Interestingly, recent years, merging these two concepts activation migratory insertion gained much attention, particular group 9 metal-catalyzed arene precursors via insertion. In this review, we summarize advances direct alkylation/alkenylation/arylation also discuss intermediates within catalytic cycles.

Language: Английский

Citations

66
In-silico molecular modelling, MM/GBSA binding free energy and molecular dynamics simulation study of novel pyrido fused imidazo[4,5-c]quinolines as potential anti-tumor agents DOI Creative Commons

Upala Dasmahapatra,

Kiran Kumar Chitluri, Soumyadip Das

et al.

Frontiers in Chemistry, Journal Year: 2022, Volume and Issue: 10

Published: Sept. 30, 2022

With an alarming increase in the number of cancer patients and a variety tumors, it is high time for intensive investigation on more efficient potent anti-tumor agents. Though numerous agents have enriched literature, still there exist challenges, with availability different targets possible cross-reactivity. Herein we chosen phosphoinositide 3-kinase (PI3K) as target interest investigated potential pyrido fused imidazo[4,5- c ]quinoline derivatives to bind strongly active site, thereby inhibiting progression various types tumors. The AutoDock, Glide Prime-MM/GBSA analysis are used execute molecular docking validation designed compounds. property evaluations were carried out by using PASS algorithm. Based GLIDE score, binding affinity molecules towards PI3K was evaluated. energetics associated static interactions revealed 1j most candidate dynamic investigations including RMSD, RMSF, Rg, SASA hydrogen bonding also supported same through relative stabilization induced ligand interactions. Subsequently, free energy Wortmannin complex calculated MM-PBSA analysis. Further prediction algorithm above results. studies reveal that evidence considering appropriate compounds

Language: Английский

Citations

52
Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides DOI

Pratiksha Bhorali,

Sabera Sultana, Sanjib Gogoi

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(4)

Published: March 23, 2022

Abstract In recent years, the transition‐metal‐catalyzed functionalization reactions of sulfoxonium ylides have been explored extensively because their usefulness as carbene‐transfer agents, since they can produce metal carbenes through catalysis. Moreover, are safer and advantages simple handling good stability over other counterparts like diazo‐compounds. This review article attempts to highlight advances in metal‐catalyzed C−H ylides.

Language: Английский

Citations

41
Rh(iii)-catalyzed C–H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins DOI
Chuanliu Yin, Lianghao Li, Chuanming Yu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(5), P. 1112 - 1116

Published: Jan. 1, 2022

The direct synthesis of isocoumarin skeletons has been realized through the Rh( iii )-catalyzed [3 + 3] annulation sulfoxonium ylides and iodonium under mild conditions.

Language: Английский

Citations

33
Recent advances in the synthesis of 2,3-fused quinazolinones DOI

Wang Wang,

Pei‐Sen Zou,

Li Pang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(32), P. 6293 - 6313

Published: Jan. 1, 2022

As one of the most important structural units in pharmaceuticals and medicinal chemistry, quinazolinone its derivatives exhibit a wide range biological pharmacological activities, including anti-inflammatory, antitubercular, antiviral, anticancer etc. In particular, 2,3-fused quinazolinones have attracted much attention because rings fused to 2,3-positions improve their rigidity planarity. Their synthetic strategies made great advances recent years. Therefore, this review focuses on novel for synthesis from 2017 2022, such as difunctionalization alkenes, ring-opening easily available small rings, dehydrogenative cross-coupling reactions, transition-metal catalyzed cyclizations, cycloadditions, other cascade reactions.

Language: Английский

Citations

31
Cobalt(III)-Catalyzed Chemo- and Regioselective [4 + 2]-Annulation of Aromatic Sulfoxonium Ylides with 1,3-Diynes DOI
Suresh Kumar Yadav,

Balu Ramesh,

Masilamani Jeganmohan

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(6), P. 4134 - 4153

Published: March 4, 2022

Air-stable, highly abundant, and cost-effective Co(III)-catalyzed redox-neutral [4 + 2]-annulation of aromatic sulfoxonium ylides with 1,3-diynes providing useful substituted 1-naphthol derivatives in a regioselective manner is described. Further, the prepared 1-naphthols having internal alkyne were converted into polycarbocyclic molecules spiro-dienone good-to-excellent yields. A possible reaction mechanism involving ortho C–H activation as key step was proposed supported by deuterium labeling kinetic isotope studies.

Language: Английский

Citations

22