Palladium-Catalyzed Oxidative Cyclization of O-Aryl Cyclic Vinylogous Esters: Synthesis of Benzofuran-Fused Cyclohexenones DOI Creative Commons
Ko-Wang Yen,

Chyh‐Cbung Chein,

Shih-Hsun Wung

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 28, 2024

This study presents a method for synthesizing functionalized hydrodibenzofuran derivatives. Using palladium catalysis, O-aryl cyclic vinylogous esters undergo dehydrogenative intramolecular arylation at the vinylic carbon. Preliminary kinetic isotope effect studies suggest that C(aryl)–H bond cleavage may be rate-determining step.

Language: Английский

Backbone-enabled modification of peptides with benzoquinone via palladium-catalyzed δ-C(sp2)–H functionalization DOI

Fengjie Lu,

Yi Sun, Yaning Liu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(13), P. 1754 - 1757

Published: Jan. 1, 2024

Backbone-enabled site-selective modification of peptides with benzoquinone via Pd-catalyzed δ-C(sp 2 )–H functionalization has been achieved.

Language: Английский

Citations

7
Mn-doped nickel–cobalt sulfides as bifunctional electrodes for high-performance supercapacitors and electrocatalysts for hydrogen evolution reactions DOI
Hui Xu, Siyao Li, Yuanqiang Zhu

et al.

Journal of Electroanalytical Chemistry, Journal Year: 2024, Volume and Issue: 955, P. 118048 - 118048

Published: Jan. 21, 2024

Language: Английский

Citations

7
Rh(III)‐Catalyzed Cascade Cyclization of 2‐Aryl‐3H‐indoles and CF3‐Imidoyl Sulfoxonium Ylides Toward Trifluoroacetimidoyl‐Substituted 11H‐Isoindolo[2,1‐a]indoles DOI Creative Commons

Zuguang Yang,

pinyi li,

Zhengkai Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3855 - 3860

Published: Oct. 18, 2023

Abstract A rhodium(III)‐catalyzed C−H activation/[4+1] annulation of 2‐aryl‐3 H ‐indoles and CF 3 ‐substituted imidoyl sulfoxonium ylides (TFISYs) has been achieved, producing a wide variety trifluoroacetimidoyl‐substituted 11 ‐isoindolo[2,1‐a]indoles in 51–86% yields. The cascade reaction involves imidoylmethylation, tautomerization AgOAc‐mediated C−N bond formation sequence. could be scaled up to 2 mmol scale.

Language: Английский

Citations

14
Crafting 1,4-diaryl spirobifluorene hosts in OLEDs via interannular C−H arylation: synergistic effects of molecular linearity and orthogonality DOI Creative Commons
Qian Shu Li, Zhiqian Yu, Qianhui Liu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(27), P. 10547 - 10555

Published: Jan. 1, 2024

Design concept of introducing linear structure into orthogonal configuration is presented. To validate this concept, 1,4-diaryl spirobifluorenes are synthesized via interannular selective C–H arylation, proving to be excellent pure hydrocarbon hosts.

Language: Английский

Citations

4
Ruthenium-Catalyzed Remote Trifunctionalization of Non-Activated Alkenes via Cyano Migration and meta-C(sp2)–H Functionalization DOI
Junlei Zhang, Xixi Zhao,

You-Zhi Liao

et al.

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

Published: Jan. 28, 2025

A novel Ru-catalyzed radical-triggered trifunctionalization of hexenenitriles is presented, employing a strategy remote cyano group migration and meta-C(sp2)-H functionalization. Through migration, the alkenyl moiety undergoes difunctionalization to formation benzylic radical intermediate. This intermediate facilitates para-selective C-H bond addition relative C-Ru within Ru(III) complex, ultimately enabling trifunctionalization. methodology provides an efficient route diverse array nitrile-containing compounds with broad functional compatibility.

Language: Английский

Citations

0
Construction of Biaryl Sulfonamides via Pd(II)-Catalyzed Cross-Coupling of C(sp2)-H Bonds with Iodobenzenesulfonamides DOI Creative Commons

Debabrata Bhattacharya,

S. C. Pal,

Indranil Banerjee

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: unknown

Published: April 21, 2025

Language: Английский

Citations

0
Picolinamide-assisted ortho-C–H functionalization of pyrenylglycine derivatives using aryl iodides DOI
Arup Dalal,

Subhankar Bodak,

Srinivasarao Arulananda Babu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(6), P. 1279 - 1298

Published: Jan. 1, 2024

Chemical transformations involving pyrenylglycine are seldom known. This paper reports the synthesis of C(2)-arylated (an unnatural amino acid) motifs via a Pd( ii )-catalyzed C–H functionalization and arylation in non-K-region pyrene.

Language: Английский

Citations

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

Fu‐Xiaomin Liu,

Weijie Chen, Ying Cai

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2512 - 2517

Published: Jan. 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.

Language: Английский

Citations

3
Recent advancements in metal-free C–C bond formation via C–H bond functionalization DOI

A. K. Sikder,

Jhimli Sengupta

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review delves into the peroxides or visible light induced metal-free C–H bond cleavage to accomplish C(sp/sp 2 /sp 3 )–H alkylation, alkenylation, arylation, carbonylation, carbamoylation, alkynylation and cyanation.

Language: Английский

Citations

0
Fundamental Principles in Catalysis from Mechanistic Studies of Oxidative Decarboxylative Coupling Reactions DOI
Jessica M. Hoover

Accounts of Chemical Research, Journal Year: 2025, Volume and Issue: unknown

Published: May 7, 2025

ConspectusOxidative decarboxylative coupling (ODC) reactions have been recognized as powerful alternatives to traditional cross-coupling due the ability generate (hetero)biaryl structures from simple and readily available carboxylic acid precursors. These reactions, however, are underdeveloped requirement for ortho-nitrobenzoate partners silver salts oxidants. Our research program has focused on development of new catalytic ODC well mechanistic studies these uncover origin synthetic limitations. As framework studies, we explored two key developed in our group: (1) a Ni-catalyzed arylation reaction that relies oxidant (2) Cu-catalyzed thiolation capable operating under aerobic conditions. findings, disclosed this Account, uncovered importance ortho-substituent revealed Ag-based oxidants also responsible mediating decarboxylation transmetalation steps.Systematic exploration series well-defined Ag-benzoate complexes allowed us probe ortho-nitro group step. Kinetic measurements large differently substituted benzoates were found correlate with field effect (F) ortho-substituent, revealing feature be enhanced reactivity favored benzoates.Our an unexpected redox step system. Synthesis isolation proposed nickelacycle Ag-aryl intermediates enabled direct study fundamental steps. Catalytic stoichiometric complexes, paired DFT calculations, supported which intermediate transfers aryl ligand AgI NiII concomitant oxidation NiIII-bis(aryl) intermediate.Finally, detailed demonstrated how catalyst system is able use O2 terminal oxidant. synthesis copper CuI-benzoate resting state, despite oxidizing conditions could support higher state intermediates. We identified intermediacy diphenyl disulfide (PhSSPh) formed thiophenol (PhSH) partner The PhSSPh proceeds via oxidative transfer PhS fragment CuI analogous observed arylation.These combined suggest significant implications more broadly. For example, it appears important when unable (as case nickel) but not needed efficient mediator its own copper). Furthermore, plays additional role required itself (such PhSSPh). anticipate insights will facilitate operate milder broader substrate scopes.

Language: Английский

Citations

0