Sonochemistry and Copper Catalysis: An Efficient Duo in the Synthesis of Chalcogenylindolizines DOI
Filipe Penteado, Luana Bettanin,

Kethelyn Machado

et al.

Asian Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 9(10), P. 1631 - 1637

Published: July 13, 2020

Abstract Herein, we describe an efficient and selective Cu‐catalyzed C−H bond chalcogenation of the indolizine core, in presence DMSO applying ultrasound irradiation as alternative energy source. Under optimal conditions, 3‐sulfanylindolizines (16 examples) were prepared moderate to good yields starting from diorganyl disulfides 2‐arylindolizines. When diphenyl diselenide was used, 1,3‐bis(selanyl) indolizines (4 exclusively obtained very yields. The use makes reaction faster more when compared conventional heating.

Language: Английский

Electrochemical direct C–H mono and bis-chalcogenation of indolizine frameworks under oxidant-free conditions DOI

Amreen Chouhan,

Kusum Ucheniya,

Lalit Yadav

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(37), P. 7643 - 7653

Published: Jan. 1, 2023

Herein, we disclosed a sustainable electrochemical approach for site-selective C-H mono and bis-chalcogenation (sulfenylation or selenylation) of indolizine frameworks. Diversely functionalized disulfides diselenides possessing EDGs EWGs were successfully reacted with variety indolizines to directly access sulfenylated/selenylated in 40-96% yields. A mechanistic radical pathway was also validated control experiments cyclic voltammogram data.

Language: Английский

Citations

7

Synthesis of Symmetrical Diorganyl Disulfides Employing WEB as an Eco‐friendly Oxidative System DOI
Andrielli Leitemberger, Lucas Martins Correa Böhs, Clarissa H. Rosa

et al.

ChemistrySelect, Journal Year: 2019, Volume and Issue: 4(26), P. 7686 - 7690

Published: July 10, 2019

Abstract Herein, we report a straightforward and environmentally benign methodology for the preparation of symmetrical diorganyl disulfides via oxidation thiols, under open atmosphere. Water Extract Banana peel ash (WEB) was conveniently employed as selective eco‐friendly system oxidative dimerization affording corresponding in very good yields.

Language: Английский

Citations

22

Catalyst-Free Conjugate Addition of Indolizines to In Situ-Generated Oxidized Morita–Baylis–Hillman Adducts DOI
Thiago S. Silva, Lucas A. Zeoly, Fernando Coelho

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(8), P. 5438 - 5448

Published: March 20, 2020

Sequential one-pot 2-iodoxybenzoic acid (IBX) oxidation of Morita–Baylis–Hillman (MBH) adducts followed by catalyst-free indolizine conjugate addition was developed. The wide scopes MBH and indolizines were investigated, densely functionalized obtained in yields up to 94%. step occurred less than a minute at room temperature with total regioselectivity toward C3 carbon. Less nucleophilic C1 carbon also alkylated when C3-substituted employed as the substrate.

Language: Английский

Citations

19

Palladium‐Catalyzed Distal C−H Selenylation of 2‐Aryl Acetamides with Diselenides and Selenyl Chlorides DOI

Meicui He,

Linghui Gu,

Yuqiang Tan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(24), P. 5708 - 5715

Published: Oct. 27, 2020

Abstract A convenient and effective method of palladium‐catalyzed C−H selenylation the 2‐aryl acetamides assisted with removable 8‐aminoquinoline readily available diselenides selenyl chlorides has been developed. This reaction is scalable tolerates a wide range functional groups, providing straightforward way preparing unsymmetrical diaryl selenides dibenzoselene‐pinone. Preliminary mechanistic studies indicated that single‐electron transfer type mechanism facile metalation are operative. magnified image

Language: Английский

Citations

19

Recent advances in transition-metal-catalyzed (Csp2)-X (X = Se, Te, As, Sb) bond formation DOI
Laxmidhar Rout,

Papita Behera,

Tharmalingam Punniyamurthy

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 557, P. 113993 - 113993

Published: March 1, 2024

Language: Английский

Citations

2

Me3SiBr-promoted cascade electrophilic thiocyanation/cyclization of ortho-alkynylanilines to synthesize indole derivatives DOI
Qing Wang, Chukai Shao, Ruirui Hua

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(20), P. 4031 - 4035

Published: Jan. 1, 2024

A Me 3 SiBr promoted cascade electrophilic thiocyanation/cyclization of ortho -alkynylanilines with the N -thiocyanatosuccinimide to afford 3-thiocyanatoindoles has been developed.

Language: Английский

Citations

2

Regioselective deoxygenative chalcogenation of 7-azindole N-oxides promoted by I2/PEG-200 DOI
Shanshan Liu, Heng Yang, Lin‐Yu Jiao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(47), P. 10073 - 10087

Published: Jan. 1, 2019

We developed a general and sustainable approach for the regioselective deoxygenative chalcogenation of 7-azindole N-oxides; combination internal oxidant green solvent has been used synthesis mono- dichalcogenyl azaindoles.

Language: Английский

Citations

18

Boosted Heterogeneous Catalysis by Surface‐Accumulated Excess Electrons of Non‐Oxidized Bare Copper Nanoparticles on Electride Support DOI Creative Commons

Sung Su Han,

Athira Thacharon, Jun Kim

et al.

Advanced Science, Journal Year: 2022, Volume and Issue: 10(2)

Published: Nov. 17, 2022

Engineering active sites of metal nanoparticle-based heterogeneous catalysts is one the most prerequisite approaches for efficient production chemicals, but limited and undesired oxidation on nanoparticles still remain as key challenges. Here, it reported that negatively charged surface copper 2D [Ca

Language: Английский

Citations

10

Weakly coordinating group directed rhodium-catalyzed unconventional site-selective C–H olefination of indolizines at the 8-position DOI

Feng Xue,

Jiaxin Tian,

Ying Sun

et al.

Chinese Chemical Letters, Journal Year: 2020, Volume and Issue: 32(1), P. 470 - 474

Published: Feb. 21, 2020

Language: Английский

Citations

15

Synthesis of perfluoroaryl sulfides at electron-poor arenes via an S Ar step with an unexpected mechanism DOI
Hsuan‐Hung Liao, Shao‐Chi Lee,

Hsin Kao

et al.

Cell Reports Physical Science, Journal Year: 2022, Volume and Issue: 3(8), P. 101010 - 101010

Published: Aug. 1, 2022

Language: Английский

Citations

9