Recent Advances in Transition Metal-Catalyzed Ring-Opening Reaction of Aziridine DOI Creative Commons
Partha Sarathi Bera, Yafia Kousin Mirza,

Tarunika Sachdeva

et al.

Compounds, Journal Year: 2024, Volume and Issue: 4(4), P. 626 - 649

Published: Oct. 11, 2024

The smallest strained, saturated N-heterocycles, such as aziridine, can be a valuable building block in synthetic organic chemistry. Ring-opening reactions with various nucleophiles could the most important strategy to synthesize value-added molecular entities. Therefore, regioselective ring-opening of aziridines heteroatomic and carbon establish useful methodology biologically relevant β-functionalized alkylamines. regio-selective is highly dependent on substrate combination, stereochemical control challenging for Lewis acid-promoted reactions. development robust, catalytic process that assists accurate prediction regioselectivity stereochemistry desirable. Consequently, large number publications detailing distinct methods aziridine found literature. In this review, we discuss several transition metal catalyzed cross-coupling reaction protocols ring opening substituted nucleophiles.

Language: Английский

Hydrogen-Bonding Network-Enabled Terminal Selective Heteroarylation of Allenamides in Hexafluoroisopropanol DOI
Sachin Balaso Mohite, Partha Sarathi Bera, Yafia Kousin Mirza

et al.

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

Published: Feb. 21, 2025

Hexafluoroisopropanol (HFIP)-mediated terminal selective heteroarylation of allenamides has been accomplished through H-bonding network-enabled substrate activation in a robust fashion. This strategy features cascade process involving sequential nucleophilic addition followed by electrophilic heteroaromatic substitution and is well suited for late-stage functionalization complex bioactive molecules. The elucidation the underlying mechanism was achieved comprehensive combination several control experiments, kinetic studies, isotopic labeling isolation HFIP-allenamide intermediate adduct.

Language: Английский

Citations

1
Synthesis of (Z)-Allylsilanes by Cu-Catalyzed Regioselective Protosilylation of Allenes via a Single-Electron Process DOI
Min Ho Kim, S. Kim,

Yurim Lee

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 2380 - 2388

Published: Jan. 25, 2025

Language: Английский

Citations

0
Nickel-Catalyzed Branched Hydroalkylation of Alkenes with Diazo Compounds DOI

Nikita Kvasovs,

Valeriia Iziumchenko, Alistair J. Sterling

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

A nickel-catalyzed, branched-selective hydroalkylation of alkenes using diazo compounds has been developed. This protocol enables the functionalization both activated and unactivated alkenes, in directed nondirected manners. Mono-, di-, trisubstituted can be effectively transformed. Highly diastereoselective hydroalkylations have also demonstrated. The method provides a novel approach for introducing an α-carbonyl moiety to which is currently inaccessible by existing methods. Preliminary mechanistic investigations suggest carbene-type mechanism, unusual nickel catalysis.

Language: Английский

Citations

0
Nickel-Catalyzed Regio- and Stereoselective Hydroalkylation of Allenes: Exploiting the Unique Reactivity of Diazo Compounds as an Alkylating Source DOI

Ujjwal Karmakar,

Jae‐Han Bae,

Jin A Kim

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(22), P. 16570 - 16576

Published: Oct. 25, 2024

The reactivity of allenes has historically been limited with no previous examples their hydroalkylation using diazo compounds in any transition-metal catalytic framework. In this study, we present a Ni-catalyzed regio- and stereoselective reaction utilizing as alkylating agents. success method can be attributed to the use pyridine-based P,N ligand, which combines advantages both phosphine nitrogen ligands. Additionally, carbonyl group compound facilitates formation stable intermediates. Our detailed mechanistic studies reveal that proceeds through an initial interaction compound, followed by engagement allene.

Language: Английский

Citations

2
Nickel-Catalyzed Synthesis of Silaindanes via Sequential C–H Activating 1,5-Nickel Migration and C–Si Activating 1,4-Nickel Migration DOI
Donghyeon Lee,

Ikuya Fujii,

Ryo Shintani

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 907 - 916

Published: Dec. 30, 2024

Catalytic reactions involving 1,n-metal migration provide a powerful approach for the synthesis of complex molecular skeletons from simple precursors through activation unreactive bonds. In this work, nickel-catalyzed 3,3-disubstituted 1-silaindanes, silicon analogues valuable indanes, was developed by reaction 1,5-nickel via C–H bond and 1,4-nickel C–Si activation. It found that not only enabled at remote position but also controlled regioselectivity subsequent alkene insertion. The detailed mechanism investigated conducting deuterium labeling experiments DFT calculations. results obtained here demonstrate high potential catalytic nickel migrations activations useful cyclic organosilicon compounds.

Language: Английский

Citations

1
Recent Advances in Transition Metal-Catalyzed Ring-Opening Reaction of Aziridine DOI Creative Commons
Partha Sarathi Bera, Yafia Kousin Mirza,

Tarunika Sachdeva

et al.

Compounds, Journal Year: 2024, Volume and Issue: 4(4), P. 626 - 649

Published: Oct. 11, 2024

The smallest strained, saturated N-heterocycles, such as aziridine, can be a valuable building block in synthetic organic chemistry. Ring-opening reactions with various nucleophiles could the most important strategy to synthesize value-added molecular entities. Therefore, regioselective ring-opening of aziridines heteroatomic and carbon establish useful methodology biologically relevant β-functionalized alkylamines. regio-selective is highly dependent on substrate combination, stereochemical control challenging for Lewis acid-promoted reactions. development robust, catalytic process that assists accurate prediction regioselectivity stereochemistry desirable. Consequently, large number publications detailing distinct methods aziridine found literature. In this review, we discuss several transition metal catalyzed cross-coupling reaction protocols ring opening substituted nucleophiles.

Language: Английский

Citations

0