Dft Study on the Mechanism of Selectively Oxidative C(Sp2)−H/C(Sp3)−H Cross-Coupling of Benzamides with Amides by Nickel Catalyst: Oxidant-Controlled Regioselectivity DOI
Cong Zhang,

Zhenfeng Shang,

Ruifang Li

et al.

SSRN Electronic Journal, Journal Year: 2022, Volume and Issue: unknown

Published: Jan. 1, 2022

The mechanisms of Ni-catalyzed selective oxidation C(sp 2 )-H/C(sp 3 )-H cross-coupling benzamide with amide are investigated using density functional theory (DFT) calculations. we have also conducted a detailed study on the formation two different free radicals, α-C(sp ) carbon radical RA and RB that is adjacent to nitrogen atom. These theoretical insights into oxidant-controlled may inspire future discovery oxidants for coupling reactions.

Language: Английский

Recent Developments in Enantioselective Domino Reactions. Part A: Noble Metal Catalysts DOI

Hélène Pellissier

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(5), P. 620 - 681

Published: Jan. 17, 2023

Abstract This review updates the field of enantioselective domino reactions promoted by chiral catalysts derived from noble metals, including palladium, silver, rhodium, ruthenium, iridium and gold, published since beginning 2019. It illustrates how much a diversity these allow unprecedented asymmetric many types to be achieved with excellent enantioselectivity, giving direct access wide variety complex molecules. magnified image

Language: Английский

Citations

22
Transition Metal-Controlled Divergent Annulations of Azomethine Imines with Iodonium Ylides via C-Centered [1,2]-Rearrangement DOI
Jie Ren, Chao Pi, Xiuling Cui

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(15), P. 2582 - 2587

Published: April 10, 2023

Transition metal-controlled divergent annulation reactions of azomethine imines with iodonium ylides via C-centered [1,2]-rearrangement have been developed. The imino group, as a switchable and transient directing group (DG), underwent intramolecular nucleophilic addition in situ generated bicyclic diaziridine, which facilitated the subsequent annulations presence different metal complexes catalysts. benzo[c]chromen-1-one pyrano[de]isochromene scaffolds could be independently constructed Rh(III) Ru(II), respectively. It was worth noting that employed first DG through rearrangement progress.

Language: Английский

Citations

14
A divergent construction of fused and bridged carbo-/heterocyclic scaffoldsviacascade reactions of aryl azomethine imines with vinyl cyclic carbonates DOI

Xinyuan Cai,

Xia Song,

Xueying Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 1015 - 1021

Published: Jan. 1, 2023

Presented herein is a divergent synthesis of indene-fused pyrazoles and bridged benzodiazepines tethered with hydroxymethyl group through the cascade reactions aryl azomethine imines vinyl cyclic carbonates.

Language: Английский

Citations

12
Synthesis of Polysubstituted Furans: An Update Since 2019 DOI Open Access

Suhasini Mohapatra,

Jasmine Panda, Seetaram Mohapatra

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(9)

Published: Aug. 7, 2023

Abstract Polysubstituted furans are widespread structural motifs, extensively dispersed in natural products, numerous bioactive compounds, pharmaceuticals, agrochemicals and organic functional materials. Hence, the development of rapid competent methodologies for synthesis multisubstituted has drawn much attention over years. This review summarizes polysubstituted using transition‐metal catalyzed, transition metal‐free, photochemical electrochemical approaches with plausible mechanistic insights. In each reaction, highest yields di‐, tri‐ or tetrasubstituted highlighted some applications methodology towards products biologically active compounds mentioned. The present highlights recent progresses reported from 2019 to 2023.

Language: Английский

Citations

12
Concise Synthesis of Spirocyclic Dihydrophthalazines through Spiroannulation Reactions of Aryl Azomethine Imines with Cyclic Diazo Compounds DOI

Xinyuan Cai,

Xia Song,

Qiuhui Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(16), P. 11048 - 11062

Published: Aug. 3, 2022

Spiroannulation reactions are fundamental and invaluable for the synthesis of spirocyclic compounds. Presented herein novel cascade aryl azomethine imines with cyclic diazo compounds leading to formation dihydrophthalazine derivatives. Based on experimental mechanistic studies, title products is believed go through imine-assisted cylcometalation, Rh-carbene dediazonization, migratory insertion followed by reductive elimination imine ring opening. Control experiments revealed that air acts as an effective sustainable co-oxidant facilitate reaction. In general, this concise unprecedented derivatives has advantages such easily accessible substrates, good functional group compatibility, mild reaction conditions, high efficiency selectivity, excellent atom-economy. addition, value protocol underlined its ready scalability divergent derivation products.

Language: Английский

Citations

16
Construction of Rings via Metal‐Catalyzed C−H Annulation with Unsymmetrical Internal Alkynes: Selectivity and Applications DOI

Qiaoya Zhang,

Ci Chen,

Bairong Liu

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(21)

Published: Aug. 19, 2023

Abstract Selective and concise construction of ring systems that are ubiquitous skeletons across chemistry, drugs materials, is indispensable for human life. Of note, directed C−H annulation with alkynes the expedient delivery holds great importance, featuring step‐ atom‐economy, mild conditions, broad substrate scope. However, regioselectivity issues remained when using unsymmetrical annulation. Herein, we summarized recent achievements towards solving this problem by developing directing groups, metal catalysts, versatile traceless functionality ensure overall regioselectivity, enantioselectivity, efficiency, synthetic application. We hope concept will promote further development precise functional molecules alkynes.

Language: Английский

Citations

8
Synthesis of gem-difluorinated pentacyclic indenopyrazolopyrazolones via Rh(iii)-catalyzed cascade C–H functionalization/[3 + 2] dipolar cycloaddition DOI

Fu‐Xiaomin Liu,

Weijie Chen, Ying Cai

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2512 - 2517

Published: Jan. 1, 2024

A Rh( iii )-catalysed cascade C–H functionalization/[3 + 2] dipolar cycloaddition was realized to deliver gem -difluorinated pentacyclic indenopyrazolopyrazolones with four continuous chiral carbon centres in a one-pot fashion.

Language: Английский

Citations

3
Half-Sandwich d6-Metal (CoIII, RhIII, IrIII, RuII)-Catalyzed Enantioselective C–H Activation DOI Creative Commons
Pu‐Fan Qian, Jun-Yi Li, Yibo Zhou

et al.

SynOpen, Journal Year: 2023, Volume and Issue: 07(04), P. 466 - 485

Published: Sept. 6, 2023

Abstract Transition-metal-catalyzed enantioselective C–H activation provides a straightforward strategy to synthesize chiral molecules from readily available sources. In this graphical review, we summarize the progress on half-sandwich d6-metal (CoIII, RhIII, IrIII, RuII)-catalyzed functionalization reactions. The review is categorized according type of metal catalyst and ligand employed. Representative enantio-determining models catalytic cycles are presented.

Language: Английский

Citations

7
Synthesis of Polysubstituted Furan Frameworks via [3 + 2] Annulation of N-Enoxyimides with Chelated Alkynes Initiated by Rh(III)-Catalyzed C–H Activation DOI
Min Wu, Yi Wang, Jing Zhou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(14), P. 2394 - 2399

Published: April 3, 2023

A variety of 2,3,5-trisubstituted furans were synthesized by virtue a Rh(III)-catalyzed vinylic C-H coupling N-enoxyimides with propargyl alcohols or amines. In this protocol, served as one-oxygen and two-carbon synthon the -OH/-NHR moiety in alkynes was found to be crucial for realizing desired chemo-/regioselectivity. Detailed experimental mechanistic studies together DFT calculations clarified sequential activation/regioselective alkyne insertion/simultaneous O-N bond cleavage hydrogen transfer/intramolecular nucleophilic addition/aromatization reaction path, which involved distinctive Rh(V) carbene species active intermediate.

Language: Английский

Citations

4
Enantioselective Synthesis of Indole‐Derivated Axially Chiral Frameworks via CpXRh(III)‐Catalyzed Domino Cyclization/C3‐Arylation of 2‐Alkynylanilines with 1‐Diazonaphthoquinones DOI
Junwei Ye,

Qingwei Song,

Dongping Pan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1064 - 1069

Published: Jan. 13, 2024

Abstract We report herein a chiral Cp X Rh(III)‐catalyzed domino cyclization/C 3 ‐arylation process using 2‐alkynylanilines and 1‐diazonaphthoquinones as viable substrates, delivering indole‐based derivatives endowed with axial chirality. The method features high enantioselectivity, broad substrate scope, robust functional group tolerance. Subsequent functionalization of the synthesized scaffolds underlines practicality this approach in design indole‐derivated axially frameworks, demonstrating its substantial promise synthetic medicinal chemistry applications.

Language: Английский

Citations

1