Brønsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations

2009 ◽  
Vol 15 (35) ◽  
pp. 8852-8860 ◽  
Author(s):  
Wei Li ◽  
Min Shi ◽  
Yuxue Li
Keyword(s):  
Dft Calculations ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Mechanistic Investigations

Co-catalysis between DABCO and a Brønsted acid in the catalytic [4 + 2] annulation of isatin with but-3-yn-2-one and mechanistic investigations

2015 ◽  
Vol 2 (3) ◽  
pp. 211-215 ◽  
Author(s):  
Qiang Wang ◽  
Qin Xu ◽  
Min Shi
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Base Catalyst ◽  
Deuterium Labeling ◽  
Brönsted Acid ◽  
Proton Source ◽  
Mechanistic Investigations

Catalytic amounts of the base catalyst DABCO in cooperation with a proton source afford the [4 + 2] cycloadducts of isatins with but-3-yn-2-one in moderate to good yields. Moreover, related plausible mechanisms have been proposed in detail based on control and deuterium labeling experiments.

scholarly journals [1,3]/[1,4]-Sulfur atom migration in β-hydroxyalkylphosphine sulfides

2020 ◽  
Vol 16 ◽  
pp. 88-105
Author(s):  
Katarzyna Włodarczyk ◽  
Piotr Borowski ◽  
Marek Stankevič
Keyword(s):  
Dft Calculations ◽  
Lewis Acid ◽  
Sulfur Atom ◽  
Bronsted Acids ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Carbon Migration ◽  
Brönsted Acid ◽  
Atom Migration ◽  
Insight Into

β-Hydroxyalkylphosphine sulfides undergo [1,3]- or [1,4]-sulfur atom phosphorus-to-carbon migration in the presence of Lewis or Brønsted acids. The direction of sulfur atom migration depends on the type of acid used for the reaction. In the presence of a Brønsted acid, mainly [1,3]-rearrangement is observed, whereas a Lewis acid catalyzes the [1,4]-sulfur migration. To gain insight into the mechanism of these transformations, the stereochemistry of these rearrangements have been tested, along with the conduction of some control experiments and DFT calculations.

Ring-Opening Hydroarylation of Monosubstituted Cyclopropanes Enabled by Hexafluoroisopropanol

2018 ◽  
Author(s):  
Edward Richmond ◽  
Jing Yi ◽  
Vuk D. Vuković ◽  
Fatima Sajadi ◽  
Christopher Rowley ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Ring Opening ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Broad Scope ◽  
Brönsted Acid ◽  
Donor Acceptor ◽  
Addition Pathway

<div><p>Ring-opening hydroarylation of cyclopropanes is typically limited to substrates bearing a donor-acceptor motif. Here, the transformation is achieved for monosubstituted cyclopropanes by using catalytic Brønsted acid in hexafluoroisopropanol (HFIP) solvent, constituting a rare example where such cyclopropanes engage in intermolecular C–C bond formation. Branched products are obtained when electron-rich arylcyclopropanes react with a broad scope of arene nucleophiles in accord with a simple S<sub>N</sub>1-type ring-opening mechanism. In constrast, linear products are obtained when cyclopropylketones react with electron-rich arene nucleophiles. In the latter case, mechanistic experiments and DFT-calculations support a homo-conjugate addition pathway.</p></div>

Ring-Opening Hydroarylation of Monosubstituted Cyclopropanes Enabled by Hexafluoroisopropanol

2018 ◽  
Author(s):  
Edward Richmond ◽  
Jing Yi ◽  
Vuk D. Vuković ◽  
Fatima Sajadi ◽  
Christopher Rowley ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Ring Opening ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Broad Scope ◽  
Brönsted Acid ◽  
Donor Acceptor ◽  
Addition Pathway

<div><p>Ring-opening hydroarylation of cyclopropanes is typically limited to substrates bearing a donor-acceptor motif. Here, the transformation is achieved for monosubstituted cyclopropanes by using catalytic Brønsted acid in hexafluoroisopropanol (HFIP) solvent, constituting a rare example where such cyclopropanes engage in intermolecular C–C bond formation. Branched products are obtained when electron-rich arylcyclopropanes react with a broad scope of arene nucleophiles in accord with a simple S<sub>N</sub>1-type ring-opening mechanism. In constrast, linear products are obtained when cyclopropylketones react with electron-rich arene nucleophiles. In the latter case, mechanistic experiments and DFT-calculations support a homo-conjugate addition pathway.</p></div>

Designating Oxygen Anions in Al–ITQ-21 as Brønsted Acid Sites Using DFT Calculations

2015 ◽  
Vol 119 (29) ◽  
pp. 16568-16577
Author(s):  
Akimitsu Miyaji ◽  
Akinobu Shiga ◽  
Yoshihiro Hayashi ◽  
Toshiki Nishitoba ◽  
To-ru Koyama ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Acid Sites ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brønsted Acid Sites ◽  
Brönsted Acid ◽  
Brönsted Acid Sites ◽  
Bronsted Acid Sites ◽  
Oxygen Anions

Experimental and theoretical studies on glucose conversion in ethanol solution to 5-ethoxymethylfurfural and ethyl levulinate catalyzed by a Brønsted acid

2021 ◽  
Author(s):  
Shijie Wang ◽  
Yihang Chen ◽  
Yu Jia ◽  
Guizhuan Xu ◽  
Chun Chang ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Reaction Pathway ◽  
Ethanol Solution ◽  
Theoretical Studies ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Ethyl Levulinate ◽  
Alcoholysis Reaction ◽  
Brönsted Acid ◽  
Experimental And Theoretical Studies

DFT calculations combined with experiments were used to discover the mechanism and reaction pathway of the glucose alcoholysis reaction.

Brønsted Acid Catalyzed Morita-Baylis-Hillman Reaction: A New Mechanistic View for Thioureas Revealed by ESI-MS(/MS) Monitoring and DFT Calculations

2009 ◽  
Vol 15 (45) ◽  
pp. 12460-12469 ◽  
Author(s):  
Giovanni W. Amarante ◽  
Mario Benassi ◽  
Humberto M. S. Milagre ◽  
Ataualpa A. C. Braga ◽  
Feliu Maseras ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Esi Ms ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Mechanistic View

Solvent-Free Acetalization of Glycerol with n-Octanal using Combined Brønsted Acid-Surfactant Catalyst

2017 ◽  
Vol 54 (1) ◽  
pp. 54-63 ◽  
Author(s):  
Xu Li ◽  
Lan Wu ◽  
Qiong Tang ◽  
Jinxiang Dong
Keyword(s):  
Solvent Free ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid

Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

2021 ◽  
Author(s):  
Mizzanoor Rahaman ◽  
M. Shahnawaz Ali ◽  
Khorshada Jahan ◽  
Damon Hinz ◽  
Jawad Bin Belayet ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Ethyl Diazoacetate ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Catalyzed Reactions
Sign in / Sign up

Export Citation Format

Share Document