DFT Investigation for the Mechanisms of γ-Butyrolactones from Styrene and Acrylic Acid, Catalyzed by NMA*BF 4 and PhSSPh DOI Creative Commons
Bing Yang, Da‐Gang Zhou

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: Feb. 26, 2024

Abstract The reaction mechanisms of γ-butyrolactones through electrophilic addition reactions between styrene and acrylic acid, catalyzed by the 9-mesityl-10-methylacridinium ion (NMA*BF 4 ) diphenyl disulfide (PhSSPh) under 450 nm visible-light, were investigated employing M06-2X-D3/ma-def2SVP method basis set. In this study, SMD model was taken to simulate solvent effect dichloromethane. photocatalyst NMA absorbs energy photons becomes an excited state, capturing electron from styrene; This leads happened obtained cationic radical acid anion (or molecule); finally, intramolecular ring-closure process H-shift result in formation final product. computational results point out that is exothermic process; optimal path for has Gibbs free barriers 11.10 9.94 kcal/mol, respectively particular, recycling photo-catalyst cocatalyst PhSSPh also been discussed. ρ hole ele can reveal charge transfer during photo-catalytic reaction. Results would provide valuable insights into these types interaction related processes.

Language: Английский

Eosin, blue LEDs and DIPEA are employed in a simple synthesis of (poly)cyclic O,O- and N,O-acetals DOI Creative Commons
Ioannis Papadopoulos, Artemis Bosveli, Tamsyn Montagnon

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(42), P. 5494 - 5497

Published: Jan. 1, 2024

A simple photocatalytic procedure for the synthesis of (poly)cyclic O , - and N -acetals from various enol ethers, -acyl enamines or Boc-protected has been developed.

Language: Английский

Citations

3
DFT investigation for the mechanisms of γ-butyrolactones from styrene and acrylic acid, catalyzed by NMA*BF4 and PhSSPh DOI
Bing Yang, Da‐Gang Zhou

Computational and Theoretical Chemistry, Journal Year: 2024, Volume and Issue: 1237, P. 114654 - 114654

Published: May 17, 2024

Language: Английский

Citations

3
Access to Functionalized Indenes via Palladium‐Catalyzed Homolytic Cleavage of a Furan C−O Bond DOI

Kai Jiang,

Guohui Zeng,

Xinyue Xie

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3597 - 3602

Published: June 19, 2024

Abstract A photoinduced palladium‐catalyzed ring‐opening hydroarylation of furans to form functionalized indenes was achieved via an intramolecular reductive coupling aryl bromide with furan using silane as the reductant. Deuterium tracking and DFT analysis revealed a reasonable reaction pathway involving: 1) homolytic cleavage C−O bond induced by α ‐allyl radical; 2) 1,6‐H atom transfer from carbon oxygen.

Language: Английский

Citations

3
Gold‐Catalyzed Cascade Reaction of Diynamides with Allylic Alcohols: A Versatile Platform to Allenamide, 2‐Aminofuran and Bridged [2.2.2]Octadiene Derivatives DOI

Jiajin Xia,

Baolong Zhu,

Qiuling Wan

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(33)

Published: March 28, 2023

Transition metal-catalyzed divergent synthesis through alternation of the catalyst is appealing, as it provides an operationally simple way to access different valuable products, while using same reactants starting materials. Herein, a gold-catalyzed cascade reaction conjugated diynamides with allylic alcohols described. By variation catalysts, substituted allenes and furans could be obtained selectively. Mechanistic studies indicate that, after addition alcohol gold-activated diynamide, [3,3]-sigmatropic rearrangement would take place lead formation common reactive intermediate, which further convert final products Further structure has unveiled additional sequence involving intramolecular Himbert arene/allene Diels-Alder cycloaddition afford series dearomatized bearing bicyclo[2,2,2]octadiene core.

Language: Английский

Citations

5
Fully Biocatalytic Rearrangement of Furans to Spirolactones DOI Creative Commons
Yu‐Chang Liu,

Julian D. Rolfes,

Joel Björklund

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(11), P. 7256 - 7262

Published: May 15, 2023

A multienzymatic pathway enables the preparation of optically pure spirolactone building blocks. In a streamlined one-pot reaction cascade, combination chloroperoxidase, an oxidase, and alcohol dehydrogenase renders efficient cascade for conversion hydroxy-functionalized furans to spirocyclic products. The fully biocatalytic method is successfully employed in total synthesis bioactive natural product (+)-crassalactone D, as key module chemoenzymatic route yielding lanceolactone A.

Language: Английский

Citations

5
Recent Developments on the Synthesis of Oxygen- and Sulfur-containing Heterocycles and their Derivatives under Visible Light Induced Reactions DOI
Tubai Ghosh, Sougata Santra, Grigory V. Zyryanov

et al.

Current Topics in Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 25(1), P. 124 - 140

Published: July 4, 2024

Visible-light-mediated reactions have recently emerged as a powerful strategy for the synthesis of diverse organic molecules under mild reaction conditions. Usually, are performed at room temperature and thus sensitive functional groups remain unaffected. Thus, this protocol has received intense interest from academia well industries. The heterocycles, in general, much because their biological activities application therapeutics. Oxygen- Sulfur-containing heterocyclic compounds attracted attention these showed promising anti-cancer drugs, antibiotics, antifungal anti-inflammatory agents among other applications. class by efficient greener routes become an important target. This review highlights various procedures derivatives visible light-induced reactions. green aspects mechanism each procedure been discussed.

Language: Английский

Citations

1
DFT Investigation for the Mechanisms of γ-Butyrolactones from Styrene and Acrylic Acid, Catalyzed by NMA*BF 4 and PhSSPh DOI Creative Commons
Bing Yang, Da‐Gang Zhou

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: Feb. 26, 2024

Abstract The reaction mechanisms of γ-butyrolactones through electrophilic addition reactions between styrene and acrylic acid, catalyzed by the 9-mesityl-10-methylacridinium ion (NMA*BF 4 ) diphenyl disulfide (PhSSPh) under 450 nm visible-light, were investigated employing M06-2X-D3/ma-def2SVP method basis set. In this study, SMD model was taken to simulate solvent effect dichloromethane. photocatalyst NMA absorbs energy photons becomes an excited state, capturing electron from styrene; This leads happened obtained cationic radical acid anion (or molecule); finally, intramolecular ring-closure process H-shift result in formation final product. computational results point out that is exothermic process; optimal path for has Gibbs free barriers 11.10 9.94 kcal/mol, respectively particular, recycling photo-catalyst cocatalyst PhSSPh also been discussed. ρ hole ele can reveal charge transfer during photo-catalytic reaction. Results would provide valuable insights into these types interaction related processes.

Language: Английский

Citations

0