DFT studies on rhodium(iii)-catalyzed synthesis of indanones from N-methoxybenzamides via C–H activation reaction DOI
Qianqian Li, Meiju Wei

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(34), P. 16576 - 16583

Published: Jan. 1, 2022

Rh( iii )-catalyzed reaction of N -methoxybenzamides with β-trifluoromethyl-α,β-unsaturated ketones to produce different products under conditions.

Language: Английский

Enantioselective Synthesis of Indole-Fused Polycycles Bearing Four Consecutive Stereocenters via Rhodium Catalysis DOI
Ting Yu, Weiqi Liu, Beijing Chen

et al.

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

Published: Feb. 3, 2025

Indole-fused polycycles are common in natural products and bioactive molecules, yet their concise efficient synthesis remains challenging, especially for compounds with multiple stereocenters. Herein, we report the application of a chiral CpxRhIII catalyst enantioselective C–H activation/[4+2] annulation indoles bicyclic alkenes. This catalytic system exhibits high enantioselectivity broad functional group tolerance operates under benign conditions. The scope this methodology encompasses variety substrates, delivering novel polycyclic four consecutive stereocenters bridged ring good to excellent yields remarkable enantioselectivities (≤1:99 er). approach facilitates structurally diverse molecules that retain integrity while introducing chirality. More importantly, 3ab significantly inhibited proliferation CESS Kasumin-1 cells IC50 values 0.76 0.28 μM, respectively. In addition, has been demonstrated as an effective agent promoting apoptosis cells.

Language: Английский

Citations

1
Accessing 7,8-Dihydroquinoline-2,5-diones via Rh-Catalyzed Olefinic C–H Activation/[4+2] Cyclization DOI
Xueqing Liu,

Sijia Shi,

Wenqian Ding

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5136 - 5140

Published: June 7, 2024

Herein, we report a rhodium-catalyzed C–H activation/[4+2] cyclization reaction between α,β-unsaturated amides and iodonium ylides for the synthesis of novel 7,8-dihydroquinoline-2,5-diones analogues. This protocol provides series pyridones fused with saturated cycles good functional group compatibility, water air tolerance, to excellent yields under mild green conditions. Additionally, scale-up can be smoothly performed as low 0.25 mol % catalyst loading. Recycling experiments different transformation were also carried out demonstrate potential synthetic utility this protocol.

Language: Английский

Citations

8
Rhodium-Catalyzed Diastereoselective C–H Activation/[4 + 2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes DOI
Yan Wang,

Sijia Shi,

Wei Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 483 - 487

Published: Jan. 10, 2024

Herein, we report a rare example of rhodium-catalyzed C–H activation/[4 + 2] annulation alkenyl amides with bicyclic alkenes under mild and green conditions. The reactivity the rhodium catalyst in this study differed from that observed cobalt-catalyzed activation/[3 between vinylic alkenes. In addition, reaction was performed EtOH at room temperature, which also displayed excellent diastereoselectivity, good functional group tolerance, air compatibility. A series novel bridged-ring skeletons were obtained to yields. Scale-up experiments carried out 1 or 0.75 mol % catalyst, affording desired skeleton

Language: Английский

Citations

7
Synthesis of CF3-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site DOI

Manqing Wang,

Shengnan Yan,

Bin Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7828 - 7842

Published: May 22, 2024

Presented herein is a novel synthesis of CF

Language: Английский

Citations

6
Pd-catalyzed acylation and allylation of 2-alkynylanilines with 1,2-diphenylcyclopropenones and gem-difluorinated cyclopropanes: a DFT study DOI
Qianqian Li, Feiwu Chen, Meiju Wei

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We reported the mechanism of Pd-catalyzed 2-alkynylaniline synthesis into indole by acylation and allylation using density functional theory.

Language: Английский

Citations

0
Recyclable rhodium-catalyzed C–H activation/[4 + 2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight DOI

Haifang Meng,

Huiying Xu, Zhi Zhou

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(18), P. 7012 - 7021

Published: Jan. 1, 2022

A robust and convenient rhodium-catalyzed unconventionally regioselective C–H activation/[4 + 2] annulation for the synthesis of isoquinolones which are prevalent in natural products pharmaceuticals was developed.

Language: Английский

Citations

18
The synthesis of spirocyclopropane skeletons enabled by Rh(III)-catalyzed enantioselective C–H activation/[4 + 2] annulation DOI Creative Commons
Hao Wang,

Yidi Li,

Lin Huang

et al.

Chem Catalysis, Journal Year: 2023, Volume and Issue: 3(12), P. 100822 - 100822

Published: Nov. 27, 2023

Language: Английский

Citations

9
Rh-catalyzed chemo-, stereo- and regioselective C–H cascade annulation of indolyloxopropanenitriles for pyranoindoles DOI

Ramesh Kotipalli,

Undamatla Suri Babu,

Jagadeesh Babu Nanubolu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(67), P. 10137 - 10140

Published: Jan. 1, 2023

Selective annulations of alkynes represent a powerful tool for constructing multicyclic scaffolds while installing desired substitution patterns with precision. Herein, we report Rh-catalyzed unique annulation indolyl oxopropanenitrile hydroxy-alkynoates to access pyranoindole cyclic motifs, featuring enol oxygen as rare chemoselective reactive terminal. The reaction proceeds via five-membered oxy-rodacycle through C-H activation by rhodium complex guided enolic- and propargyloxy dual co-ordination enable regio- stereoselective modular assembly.

Language: Английский

Citations

8
Condition‐Controlled Divergent Synthesis of Imidazoindolone Spiroisoquinolinones fromN‐Alkoxycarboxamide Indoles and Diazo Homophthalimides DOI

Manqing Wang,

Qianting Zhou,

Xinying Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(8), P. 1255 - 1261

Published: March 24, 2023

Abstract Presented herein is a condition‐controlled divergent synthesis of imidazoindolone spiro‐isoquinolinones (IISIQs) via the cascade reactions N ‐alkoxycarboxamide indoles with diazo homophthalimides. When reaction carried out under air and in absence an acid additive, IISIQ tethered ‐alkoxy moiety (IISIQ‐OR) formed through Rh(III)‐catalyzed C−H/N−H metalation, carbene formation/ migratory insertion followed by reductive elimination, which acts as oxidant to regenerate Rh(III) catalyst. run argon presence MesCO 2 H, on other hand, IISIQ−H rhodacycle intermediate formation, acid‐assisted intramolecular substitution/annulation N−O bond cleavge. In general, this method provides approach toward spiroheterocyclic scaffolds features accessible substrates, functional group compatibility external oxidant. Moreover, value developed protocol further showcased gram‐scale structural transformation products. magnified image

Language: Английский

Citations

7
Rhodium-catalyzed regioselective C–H activation/Lossen rearrangement/annulation for the green synthesis of trisubstituted 2-pyridones DOI Creative Commons

Yidi Li,

Huiying Xu, Lin Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(12), P. 3000 - 3009

Published: Jan. 1, 2023

A green and novel approach for the synthesis of 2-pyridone derivatives by a rhodium-catalyzed C–H activation/Lossen rearrangement acrylamides propargyl alcohols is reported.

Language: Английский

Citations

7