scholarly journals Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol

2018 ◽  
Vol 9 (30) ◽  
pp. 6411-6416 ◽  
Author(s):  
Edward Richmond ◽  
Jing Yi ◽  
Vuk D. Vuković ◽  
Fatima Sajadi ◽  
Christopher N. Rowley ◽  
...  
Keyword(s):  
Ring Opening ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Donor Acceptor

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.

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>

Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes

2021 ◽  
Author(s):  
Alesandere Ortega ◽  
Uxue Uria ◽  
Tomás Tejero ◽  
Liher Prieto ◽  
Efraim Reyes ◽  
...  
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Donor Acceptor ◽  
Acid Catalyzed

2,4-Dinitrobenzenesulfonic acid in an efficient Brønsted acid-catalyzed controlled/living ring-opening polymerization of ε-caprolactone

RSC Advances ◽  
2014 ◽  
Vol 4 (99) ◽  
pp. 55716-55722 ◽  
Author(s):  
Huiying Wang ◽  
Wenzhuo Wu ◽  
Zhenjiang Li ◽  
Xu Zhi ◽  
Cheng Chen ◽  
...  
Keyword(s):  
Ring Opening ◽  
Diblock Copolymers ◽  
Ring Opening Polymerization ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Acidic Catalyst ◽  
Brönsted Acid ◽  
Acid Catalyzed

2,4-Dinitrobenzenesulfonic acid as an efficient Brønsted acidic catalyst has been evaluated for the controlled/living ring-opening polymerization of ε-caprolactone end-functionalized, α,ω-dihydroxy telechelic poly(ε-caprolactone), and diblock copolymers were also synthesised successfully.

Brønsted acid-catalysed intramolecular ring opening of 2-(aryloxymethyl)-3-aryloxiranes leading to trans-4-arylchroman-3-ols: scope and limitations

RSC Advances ◽  
2015 ◽  
Vol 5 (50) ◽  
pp. 39692-39696 ◽  
Author(s):  
Runjun Devi ◽  
Tapasi Kalita ◽  
Sajal Kumar Das
Keyword(s):  
Ring Opening ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Metal Free ◽  
Brönsted Acid ◽  
Intramolecular Ring

A simple and metal-free method for the synthesis of a series oftrans-4-arylchroman-3-olsviaBrønsted acid-catalysed stereoselective intramolecular Friedel–Crafts alkylation of electron-rich arenes by tethered epoxides is developed.

Lewis and Brønsted Acid Induced (3 + 2)-Annulation of Donor–Acceptor Cyclopropanes to Alkynes: Indene Assembly

2015 ◽  
Vol 17 (4) ◽  
pp. 770-773 ◽  
Author(s):  
Eduard R. Rakhmankulov ◽  
Konstantin L. Ivanov ◽  
Ekaterina M. Budynina ◽  
Olga A. Ivanova ◽  
Alexey O. Chagarovskiy ◽  
...  
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Donor Acceptor
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