Elucidating the Mechanism and Selectivities of Cobalt‐Catalyzed Transformation of O‐Acyl Oxime DOI Open Access
Xiaohan Yu, Yang Wang

Applied Organometallic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 19, 2024

ABSTRACT In this work, the mechanistic investigation on cobalt‐catalyzed CH functionalization of O ‐acyl oxime and verification origin selectivities are employed using density functional theory (DFT) method. Based calculations, most energetically favorable pathway contains four steps: coordination Co(III) species to oxime, para ‐selective activation give a five‐membered cobaltacycle, [2,1]‐alkyne insertion, redox‐cyclization final product regenerate species. IRC calculations clearly indicate that process occurs in concerted but highly asynchronous manner. The structural analysis reveals ‐CH preferentially mainly due less steric hindrance. FMO energetic span model used disclose regioselectivity chemoselectivity, respectively.

Language: Английский

DFT study on isothiourea-catalyzed C–C bond activation of cyclobutenone: the role of the catalyst and the origin of stereoselectivity DOI

D.C. Li,

Yang Wang

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(13), P. 2662 - 2669

Published: Jan. 1, 2024

The mechanism of organocatalytic C-C bond activation have been theoretically investigated.

Language: Английский

Citations

9

Mechanistic studies on an isothiourea-catalyzed reaction of an aromatic ester with an imine DOI

Meng-Qing Yang,

Yang Wang

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 567, P. 114445 - 114445

Published: Aug. 10, 2024

Language: Английский

Citations

4

Theoretical Investigation on A Chiral Brønsted acid (CBA)-Catalyzed Isomerization Reaction of BCB: Mechanism and Origin of Stereoselectivity DOI

Yu-Nuo Wang,

Yang Wang

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(25), P. 11360 - 11365

Published: Jan. 1, 2024

The mechanism, role of catalyst and origin stereoselectivity for the isomerization reaction BCB catalyzed by a chiral Brønsted acid (CBA) have been revealed in detail using DFT calculations.

Language: Английский

Citations

3

Theoretical investigation on the reaction mechanism and origin of stereoselectivity of a three-component coupling reaction under organocatalysis DOI

Yujian Yu,

Lujun Zhang, Yang Wang

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 573, P. 114819 - 114819

Published: Jan. 6, 2025

Language: Английский

Citations

0

Mechanistic studies on phosphine-catalyzed [4 + 3] annulation of β′-acetoxy allenoate with 1C,3N-dinucleophile DOI

Kui Yuan,

Haoran Yang, Yang Wang

et al.

Computational and Theoretical Chemistry, Journal Year: 2024, Volume and Issue: 1241, P. 114924 - 114924

Published: Oct. 19, 2024

Language: Английский

Citations

1

DFT Study on the Mechanism of Phosphine-Catalyzed Ring-Opening Reaction of Cyclopropyl Ketone DOI
Xiaohan Yu, Yang Wang

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

In the present study, mechanism, origin of chemoselectivity, and substituent effects phosphine-catalyzed ring-opening reaction cyclopropyl ketone have been investigated using DFT method. Multiple pathways, including formation hydrofluorenone, Cloke-Wilson product, cyclopenta-fused were studied compared. The computational results show that pathway for hydrofluorenone is most favorable one, which involves four processes: nucleophilic substitution to open three-membered ring, an intramolecular Michael addition enolate intermediate, [1,5]-proton transfer give ylide, Wittig deliver final product. For disclosing structural analysis local reactivity index performed. Moreover, also considered QTAIM analysis. current study would provide useful insights understanding chemoselective reactions.

Language: Английский

Citations

1

DABCO-catalyzed mono- and bisallylation of β,γ-unsaturated ketones with Morita-Baylis-Hillman carbonates DOI
Guizhou Yue,

Biao Du,

Qiumi Wang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(35), P. 15446 - 15451

Published: Jan. 1, 2024

Mono- and bisallylation of β,γ-unsaturated ketones with MBH carbonates in the presence DABCO at rt, offered α-2-alkoxycarbonyl, α,α-di(2-alkoxycarbonyl) α,γ-di(2-alkoxycarbonyl) α,β-unsaturated moderate to excellent yields.

Language: Английский

Citations

0

DFT Study in An Asymmetric Organocatalytic Homologation: Mechanism, Origin of Stereoselectivity DOI
Yang Wang, Donghui Wei

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 24, 2024

Abstract In the present study, mechanism, origin of stereoselectivity, and role catalyst organocatalytic homologation reaction between phenyl boronate trifluoromethyl diazomethane have been theoretically investigated using density functional theory (DFT) method. Based on calculations, in situ generated ethanol plays significant triggering reaction. Moreover, [1,2]‐boron migration process is stereoselectivity‐determining step, with S ‐configured isomer being predominantly. addition, NCI analysis performed to disclose stereoselectivity.

Language: Английский

Citations

0

Elucidating the Mechanism and Selectivities of Cobalt‐Catalyzed Transformation of O‐Acyl Oxime DOI Open Access
Xiaohan Yu, Yang Wang

Applied Organometallic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 19, 2024

ABSTRACT In this work, the mechanistic investigation on cobalt‐catalyzed CH functionalization of O ‐acyl oxime and verification origin selectivities are employed using density functional theory (DFT) method. Based calculations, most energetically favorable pathway contains four steps: coordination Co(III) species to oxime, para ‐selective activation give a five‐membered cobaltacycle, [2,1]‐alkyne insertion, redox‐cyclization final product regenerate species. IRC calculations clearly indicate that process occurs in concerted but highly asynchronous manner. The structural analysis reveals ‐CH preferentially mainly due less steric hindrance. FMO energetic span model used disclose regioselectivity chemoselectivity, respectively.

Language: Английский

Citations

0