Synthesis of Diarylselenides through Rh-Catalyzed Direct Diarylation of Elemental Selenium with Benzamides DOI
Qing‐Feng Xu‐Xu, Yuji Nishii, Masahiro Miura

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(24), P. 16887 - 16894

Published: Dec. 1, 2022

Diarylselenides are a representative class of molecules in organoselenium compounds. We herein report Rh-catalyzed direct diarylation selenium with benzamide derivatives. The use elemental as the Se source is intriguing terms atom economy, cost, stability, and handling. A series diarylselenides amide moieties were readily accessible through directed C-H activation. intermediacy electrophilic Se(IV) species was indicated by control experiments.

Language: Английский

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis DOI Open Access

Juan M. Sonego,

Sheila I. de Diego,

Sergio H. Szajnman

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(52)

Published: June 28, 2023

Abstract Selenium, originally described as a toxin, turns out to be crucial trace element for life that appears selenocysteine and its dimer, selenocystine. From the point of view drug developments, selenium‐containing drugs are isosteres sulfur oxygen with advantage presence selenium atom confers antioxidant properties high lipophilicity, which would increase cell membrane permeation leading better oral bioavailability. In this article, we have focused on relevant features atom, above all, corresponding synthetic approaches access variety organoselenium molecules along proposed reaction mechanisms. The preparation biological selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, other compounds will treated. We attempted condense most important aspects interesting examples chemistry into single article.

Language: Английский

Citations

52
2-Pyridone-Directed CuII–Catalyzed General Method of C(sp2)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study DOI
Tanmay K. Pati,

Sabir A. Molla,

Narendra Nath Ghosh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 6798 - 6812

Published: April 25, 2024

We have demonstrated N-substituted 2-pyridones as an N,O-directing group for selective C(sp2)-H-activated thiolation, selenylation, and sulfonamidation of ortho C–H bonds benzamides. This method utilizes a cost-effective Cu(II)-salt catalyst instead precious metal catalysts, achieving high yields, including gram-scale synthesis excellent functional tolerance. applied this protocol to access 30 different compounds with demonstrating thiolation fluorine-substituted benzamides well. Density theory (DFT) calculations support the mechanism, acetate-supported concerted metalation deprotonation (CMD) steps unique role dimethyl sulfoxide (DMSO) solvent. The facile pharmaceutically important sulfonamides other highlights method's potential in chemistry medicinal chemistry.

Language: Английский

Citations

4
Ruthenium(II)-Catalyzed C–H Activation/Annulation of 5-Phenyl-pyrroline-2-carboxylates with Alkynes: Synthesis of 2,3-Diphenylspiro-[indene-1,2′pyrrolidine]carboxylate Derivatives DOI

Anushka Rastogi,

Andrew Shaw,

Suruchi Kumari

et al.

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

Published: May 8, 2025

While saturated nitrogen heterocycles are privileged scaffolds, their streamlined catalytic synthesis with unsymmetrical substitution patterns remains a daunting challenge. Herein, we report the ruthenium(II)-catalyzed of spiro[indene-proline] derivatives via C-H activation/annulation 5-phenyl-pyrroline-2-carboxylates alkynes. The protocol utilized imine coordination, resulting in high reaction yields wide range functional group tolerance, scalability, and scaffold diversity. This annulation was successful even various biologically active pharmacophores. featured reversible metalation step suggested possibility base-assisted internal electrophilic pathway.

Language: Английский

Citations

0
Cu(II)-Catalyzed, Site Selective Sulfoximination to Indole and Indolines via Dual C–H/N–H Activation DOI
Mohit Kumar,

Anushka Rastogi,

Raziullah

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(48), P. 8729 - 8734

Published: Nov. 29, 2022

A copper-catalyzed protocol furnishing N-arylated sulfoximines has been developed via dual N-H/C-H activation. Arylalkyl- and less reactive diarylsulfoximines were efficiently coupled with privileged scaffolds like indolines, indoles, N-Ar-7-azaindoles. Sulfoximines based on medicinally relevant (phenothiazine, dibenzothiophene, thioxanthenone) also well tolerated. Detailed mechanistic studies indicate that the deprotometalation protodemetalation step is reversible step.

Language: Английский

Citations

10
Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate DOI
Jing Zhang,

Quanjian Luo,

Han‐Chi Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(9), P. 985 - 989

Published: Dec. 26, 2023

Comprehensive Summary A Ru(II)‐catalyzed ortho allylation reaction of N ‐aryl‐7‐azaindole with readily available 2‐methylidene cyclic carbonate has been developed. This is an effective pathway for synthesizing 7‐azaindole derivatives a wide scope substrates and high yields. In addition, the method can be extended to other heterocyclic compounds several carbonates, highlighting practicality this strategy synthesis.

Language: Английский

Citations

4
Copper‐Promoted Oxidative Amide‐Assisted Radical Selenylation of Anilides and N‐Arylsulfonamides with Diselenides DOI
Lou Shi,

Penghui Xu,

Yingchun Ma

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: March 21, 2024

Abstract A direct selenylation of N ‐arylsulfonamides and anilides using environmentally friendly readily available copper promoted assisted by amide is presented. This method provided convenient access for various reactions, demonstrating a wide range substrates strong tolerance to functional groups. According the selection reaction substrates, products can be isolated obtain regioselectivity ortho ‐, para or unprecedented , ‐diselenylation products. Such transformation was elucidated proposed copper‐promoted amide‐assisted radical mechanism.

Language: Английский

Citations

1
I2/DMSO Mediated Direct Selenylation of Uracils with Diorganoyl Diselenides – A Simple Protocol to Access 5‐Selanyl‐Uracils DOI
Maria Eduarda C. Thedy, Mylena Mendes Gularte, Juliano B. Azeredo

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(21)

Published: June 3, 2024

Abstract This study demonstrates a direct and regioselective selenylation protocol of unprotected uracils with diorganoyl diselenides using equivalent amount DMSO as oxidant minimum solvent, under catalysis by molecular iodine. methodology tolerates broad scope functional groups to provide several 5‐organoseleno‐substituted uracil derivatives in good excellent yields.

Language: Английский

Citations

1
Regioselective C–H chalcogenylation and halogenation of arenes and alkenes under metal-free conditions DOI
Bin Li,

Mingli Hu,

Jun Ge

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(14), P. 2910 - 2916

Published: Jan. 1, 2023

The reactions of direct Csp 2 –H chalcogenylation and halogenation N -arylpyrrolidone under the action PIFA without a directing group metal-free conditions were reported in this paper.

Language: Английский

Citations

3
Palladium-Catalyzed C(sp3)–H Biarylation of 8-Methyl Quinolines with Cyclic Diaryliodonium Salts to Access Functionalized Biaryls and Fluorene Derivatives DOI
Naveen Kumar Maurya, Suman Yadav,

Dhananjay Chaudhary

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 13744 - 13749

Published: Oct. 5, 2022

Herein, we have developed the cyclic diaryliodonium salts as biarylating agents in C(sp3)–H functionalization using 8-methyl quinoline intrinsic directing group. The oxidant-free reaction produces a vast array of biarylated products with iodo functionality that can be further functionalized. Additionally, intramolecular stepwise manner under palladium-catalyzed conditions produced fluorene derivatives excellent yields.

Language: Английский

Citations

5
Directing Group Assisted Copper‐Catalyzed C−H sulfanylation of Alkenyl Carbonyl Compounds with Disulfides DOI

Yan‐Mei Bai,

Lu‐Lu Ai,

X. Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(8)

Published: Feb. 2, 2024

Abstract A highly efficient and straightforward copper‐catalyzed sulfanylation of acrylamides with readily available disulfides has been developed. Through 8‐aminoquinoline‐assisted activation the alkenyl C−H bond, a broad scope ( Z )‐alkenyl sulfides were constructed in moderate to excellent yields good compatibility functional groups. Moreover, bidentate directing auxiliary promotes high regioselectivity )‐ β ‐alkenyl sulfides, enables performance copper catalyst this transformation.

Language: Английский

Citations

0