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

Concise preparation of daldiquinone via palladium-catalyzed regioselective peri-C-H oxygenation of the naphthalene ring DOI Creative Commons
Jing Jiang,

Yue Gao,

Chenqi Wu

et al.

Journal of Chemical Research, Journal Year: 2025, Volume and Issue: 49(1)

Published: Jan. 1, 2025

A total synthesis of the natural polycyclic phenolic compound daldiquinone was reported derived from 1-naphthaldehyde. The utilizes regioselective peri-C-H oxidation as a key step, proceeding through longest linear sequence seven steps with an overall yield 40%. binaphthol intermediate is obtained via Baeyer-Villiger oxidative rearrangement in 81% yield, followed by IBX to produce naphthoquinone. binaphthalene core constructed using Suzuki coupling. This strategy, which relied on direct C-H bond naphthalene ring, significantly truncated synthetic pathway and boosted efficiency. regiospecific approach offers promising for obtaining wide array derivatives.

Language: Английский

Citations

0
Pd(II)‐Catalyzed C3‐Alkylation and Annulation of Indole‐2‐carboxamides with Maleimides: Access to Fused β‐Carbolinone Frameworks DOI

Srinivasa Rao Kancharla,

Syeda Fatima Zeenath,

Rajashaker Bantu

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(21)

Published: June 1, 2025

Abstract A temperature‐controlled oxidative addition and annulation of maleimides onto 1H‐indole‐2‐carboxamides has been developed to the synthesis angularly fused β‐carbolinone frameworks using Pd(OAc) 2 as a catalyst Cu(OAc) co‐oxidant. It is novel atom‐economical method for one‐pot highly functionalized β‐carbolinones. modular approach 3‐(indol‐3‐yl)maleimides beta‐carbolines by mere change in temperature. This offers several advantages such operational simplicity, cleaner reaction profiles, wide substrate scope high functional group tolerance. first report on β‐carbolines through C─H bond activation 1H‐indole‐2‐carboxamides.

Language: Английский

Citations

0
Modular Assembly of Pyrrolo[3,4-c]isoquinolines through Rh-Catalyzed Cascade C–H Activation/Annulation of O-Methyl Aryloximes with Maleimides DOI

Yinsong Wu,

Yanan Liu,

Yangzilin Kong

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8447 - 8457

Published: June 4, 2024

An efficient and practical strategy for the construction of pyrrolo[3,4-

Language: Английский

Citations

3
Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles DOI

Jinfang Zhao,

Chao Pi, Yangjie Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1840 - 1846

Published: Feb. 8, 2024

Abstract Herein, we report a chemo‐ and regioselective Rh‐catalyzed redox C7‐spiroannulation reaction of N ‐benzo[ d ]imidazole indolines with maleimides, resulting in series indoline fused azaspirocycles up to 92% yield. The synthetic utility is demonstrated by the synthesis highly functionalized nitrogen‐containing spiropolycyclic skeletons. annulation could also be performed maleic esters acrylates. products were purified simple filtration. Rh catalyst can recycled, at gram‐scale using 0.5 mol% catalyst, which makes this protocol potentially applicable industry. Moreover, efficient post‐modification pharmaceutical molecules demonstrates its practicability.

Language: Английский

Citations

2
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
Pd(II)-catalyzed hydroxy group directed synthesis of spiro-fused succinimide isochromenochromenones DOI

Kongkona Gogoi,

Bondana Bora,

Geetika Borah

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: unknown, P. 155434 - 155434

Published: Dec. 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