Stereo and Regioselective Addition of N-Heterocycles on Internal Alkynes Through C-N Bond Formations DOI

Nagaraj Sabarinathan,

Ganesh Udari,

Balasubramanian Sridhar

et al.

Published: Jan. 1, 2024

We report, regio and stereoselective addition of N-heterocycles on internal alkynes through C(sp2)-N(sp3) bond formation. have synthesized a series 1H-Indole, 1H-Benzimidazole Tetrahydroquinolines (THQ) functionalized Maleate, Fumarate Acrylate derivatives N- alkenylation reactions. demonstrated the selective formation E- Isomers. Further substrate dependent E Z isomers are also observed.

Language: Английский

Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds DOI

Qinhui Wan,

Zhongyi Zhang,

Zhong‐Wei Hou

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(11), P. 2830 - 2848

Published: Jan. 1, 2023

Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds and their mechanistic insights synthetic applications have been summarized.

Language: Английский

Citations

79
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
Orthogonal Synthesis of Cationic Azatriphenylene Derivatives for Aggregation-Induced Emission (AIE) and Aggregation-Caused Quenching (ACQ) Property Switching DOI Creative Commons

Yushi Ohno,

Tsukasa Ehara,

Kosuke Sato

et al.

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

Published: May 4, 2025

Herein, we report a divergent synthesis of cationic azatriphenylene derivatives using orthogonal control thermal and electro-oxidative pyridination, which transforms the single precursor into controlled products with perfect selectivity. Simultaneously, two switchable reactions afford corresponding pyridinium salts different optical properties such as aggregation-induced emission (AIE) aggregation-caused quenching (ACQ) effects.

Language: Английский

Citations

0
Radical strategies for chemodivergent cyclization reactions DOI

Ling‐Tao Wang,

Bo Zhou,

Fa-Liang Liu

et al.

Trends in Chemistry, Journal Year: 2023, Volume and Issue: 5(12), P. 906 - 919

Published: Nov. 7, 2023

Language: Английский

Citations

9
Iodine-Mediated C2,3–H Aminoheteroarylation of Indoles DOI

Maoyi Dai,

Yingying Zhang, Xiaoxiang Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15106 - 15117

Published: Oct. 21, 2023

A metal-free one-pot oxidative cross-dehydrogenation coupling reaction for the formation of C-N/C-C bonds at C2,3-positions indoles with azoles and quinoxalinones has been developed. The proposed method several notable features, including catalysis, use N-H free as substrates, ease operation, mild conditions, compatibility a wide range substrates.

Language: Английский

Citations

8
Mn(OAc)3-Promoted Sulfonation–ipso-Cyclization Cascade via the SO3– Radical: The Synthesis of Spirocyclic Sulfonates DOI
Yan Zhang,

Bingxu Han,

Xin Gu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 14140 - 14155

Published: Sept. 18, 2023

A radical sulfonation–ipso-cyclization cascade promoted by Mn(OAc)3·2H2O using functionalized alkynes or alkenes and potassium metabisulfite (K2S2O5) is reported. total of 30 spirocyclic sulfonates were synthesized under mild conditions. We also demonstrate a modular synthesis approach in multiple steps for the preparation various azaspiro[4,5]-trienone-based sulfonamides sulfonate esters.

Language: Английский

Citations

6
A microwave-assisted intramolecular aminopalladation-triggered domino sequence: an atom economical route to 5,10-dihydroindeno[1,2-b]indoles DOI

Tanvi Jandial,

Anish Gupta,

Gowsia Jan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(15), P. 3121 - 3131

Published: Jan. 1, 2023

A microwave-assisted, palladium(II)-catalyzed cascade reaction of 2-alkynylanilines tethered with an α,β-unsaturated carbonyl moiety was established to access 5,10-dihydroindeno[1,2-b]indoles in high yields (up 84%) a short time. This operationally simple process shows 100% atom economy and allows the construction two new five-membered rings (1 C-C 1 C-N) bonds single synthetic attempt. The mechanistic pathway this is visualized involving intramolecular aminopalladation (5-endo-dig) followed by carbopalladation (olefin insertion) protonolysis steps. systematic comparison between microwave irradiation conventional heating methods also performed demonstrate supremacy microwave-assisted approach. domino requires no protecting groups for amino group palladium catalyst needs ligands. To best our knowledge, first report on nucleopalladation-initiated transformation.

Language: Английский

Citations

5
Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis DOI
Wei Zhou, Xi Chen, Lin Lu

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(4), P. 108902 - 108902

Published: Aug. 9, 2023

Language: Английский

Citations

5
Chemodivergent Photocatalyzed Heterocyclization of Hydrazones and Isothiocyanates for the Selectivity Synthesis of 2-Amino-1,3,4-thiadiazoles and 1,2,4-Triazole-3-thiones DOI

Qing‐Hu Teng,

Fenglai Lu, Kai Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7104 - 7116

Published: May 4, 2023

A photocatalytic chemodivergent reaction for the selectivity formation of C-S and C-N bonds in a controlled manner was proposed. The medium, either neutral or acidic, is critical to dictate 2-amino-1,3,4-thiadiazoles 1,2,4-triazole-3-thiones from isothiocyanates hydrazones. This practical protocol achieve chemoselectivity under mild metal-free conditions.

Language: Английский

Citations

4
Cascade Electrochemical Aerobic Oxygenation of 2-Substituted Indoles and Electrochemical [5 + 3] Annulation with Amidines: Access to Eight-Membered Benzo[1,3,5]triazocin-6(5H)-ones DOI

Weihui Zhuang,

Fengyi Xiao,

Yumei Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4673 - 4683

Published: March 13, 2024

The cascade electrochemical C3-selective aerobic oxygenation of 2-substituted indoles and [5 + 3] annulation with amidines through an undivided cell galvanostatic method employing molecular oxygen "electricity" as green oxidants was developed. This protocol provides efficient direct approach to eight-membered benzo[1,3,5]triazocin-6(5H)-ones. Mechanistic studies suggested that two subsequent processes both proceeded radical pathways.

Language: Английский

Citations

1