Controlled Ru (II) & Rh (III) catalyzed [4+2] & [4+1] carbo‐annulation via C–H Activation using Sulfoxonium ylide & Maleimide: Facile access to Fused Benzoisoindole & Spiroindanone DOI

Raju Vaggu,

Akhila Muraharikar,

Y. Prasanna Kumar

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(47)

Published: Sept. 13, 2024

Abstract A well‐ordered strategy of sulfoxonium ylides as a directing group well carbene source for the Ru‐catalysed [4+2] and Rh‐catalysed [4+1] carbo‐annulations with maleimides has been described. These novel methodologies have successfully established synthesis complex spiroindanones benzoisoindoles containing compounds by transition metal‐mediated C−H activation/functionalization reactions. Further, annulated were obtained in absence any oxidant. possible rationale remarkable divergent selectivity between two catalysts proposed.

Language: Английский

Ru(II)-Catalyzed C–H Activation/[4+2] Annulation of Sulfoxonium Ylide with Maleimide: Access to Fused Benzo[e]isoindole-1,3,5-trione DOI
Dattatraya H. Dethe, Vimlesh Kumar, Rahul Das

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6830 - 6834

Published: Aug. 5, 2024

A ruthenium-catalyzed C-H activation and a concomitant [4+2] annulation of sulfoxonium ylide with maleimide have been demonstrated. This tandem reaction results in the formation fused benzo[

Language: Английский

Citations

4
Rh(III)-catalyzed [4+1] annulation of sulfoxonium ylide with allyl alkyl ethers: A detailed theoretical study of DFT, anti-inflammatory and antidiabetic activity DOI

Pakkirisamy Sivakumar,

Pothapragada S. K. Prabhakar Ganesh,

P. Muthuraja

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(36), P. 15989 - 15999

Published: Jan. 1, 2024

The [4+1] annulation of sulfoxonium ylides with allyl ether, catalyzed by Rh( iii ), efficiently produces alkyl-substituted indanone a broad substrate scope and excellent yield.

Language: Английский

Citations

4
Rh(III)-Catalyzed Redox-Neutral C–H Activation/Annulation of Oxadiazolones with Sulfoxonium Ylides to access oxadiazoloisoquinolinone DOI

Pothapragada S. K. Prabhakar Ganesh,

Eswaran Kamaraj,

Vairaperumal Veeramani

et al.

New Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Oxadiazolone-fused isoquinolines were synthesized via Rh( iii )-catalyzed [4+2] annulation and C–H activation, followed by acymethylation products with antidiabetic anti-inflammatory potential.

Language: Английский

Citations

0
Comparison of Phosphonium and Sulfoxonium Ylides in Ru(II)-Catalyzed Dehydrogenative Annulations: A Density Functional Theory Study DOI Creative Commons

Wei Zhou,

Lei Zhang, Dan-Yang Liu

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(9), P. 1883 - 1883

Published: April 23, 2025

Density functional theory calculations have been performed to explore the detailed mechanism of a ruthenium-catalyzed dehydrogenative annulation between α-carbonyl phosphonium ylide (A) and sulfoxonium (B). The proposed catalytic cycles consist several elementary steps in succession, namely C–H activation A, insertion B, reductive elimination, protodemetallation, an intramolecular Wittig reaction, which is rate-limiting, with free energy barrier 31.7 kcal/mol. As A B are both capable being substrate carbene precursor, there potentially four competing pathways including homo-coupling reactions. Further demonstrate that more reactive step than while opposite conclusion true for step, can successfully explain fact solely observed product originated from use as precursor. Molecular electrostatic potential, charge decomposition, electron density difference analyses were understand distinct behaviors two ylides nature key ruthenium–carbene intermediate.

Language: Английский

Citations

0
Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles DOI

Dattatri,

Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: March 20, 2024

Abstract We report herein a palladium‐catalyzed, site‐selective cyclative annulation of o ‐alkynyl arylamides with maleimide for the stereoselective construction succinimide‐fused benzoxazine derivatives. This operationally simple and modular protocol provides access to polycyclic frameworks. The other associated features are high functional group compatibility, gram‐scale synthetic potential, downstream transformations. Control labeling experiments were conducted get insights into mechanism.

Language: Английский

Citations

1
Reactions with sulfoxonium ylides using metal-catalysis DOI
Marcio Hayashi, Viktor Saraiva Câmara,

Cristhian S. Oliveira

et al.

Advances in organometallic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 227 - 286

Published: Jan. 1, 2024

Language: Английский

Citations

0
Controlled Ru (II) & Rh (III) catalyzed [4+2] & [4+1] carbo‐annulation via C–H Activation using Sulfoxonium ylide & Maleimide: Facile access to Fused Benzoisoindole & Spiroindanone DOI

Raju Vaggu,

Akhila Muraharikar,

Y. Prasanna Kumar

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(47)

Published: Sept. 13, 2024

Abstract A well‐ordered strategy of sulfoxonium ylides as a directing group well carbene source for the Ru‐catalysed [4+2] and Rh‐catalysed [4+1] carbo‐annulations with maleimides has been described. These novel methodologies have successfully established synthesis complex spiroindanones benzoisoindoles containing compounds by transition metal‐mediated C−H activation/functionalization reactions. Further, annulated were obtained in absence any oxidant. possible rationale remarkable divergent selectivity between two catalysts proposed.

Language: Английский

Citations

0