Brønsted acid-mediated ring-opening reactions of methylenecyclopropanes: a dramatic counter ion effect

Tetrahedron ◽  
2004 ◽  
Vol 60 (51) ◽  
pp. 11895-11901 ◽  
Author(s):  
Li-Xiong Shao ◽  
Jin-Wen Huang ◽  
Min Shi
Keyword(s):  
Ring Opening ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Counter Ion ◽  
Brönsted Acid ◽  
Ring Opening Reactions

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>

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.

Coordination polymers with free Brønsted acid sites for selective catalysis

2015 ◽  
Vol 39 (2) ◽  
pp. 810-812 ◽  
Author(s):  
Lu-Fang Ma ◽  
Zhen-Zhen Shi ◽  
Fei-Fei Li ◽  
Jian Zhang ◽  
Li-Ya Wang
Keyword(s):  
Coordination Polymers ◽  
Acid Sites ◽  
Epoxide Ring ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brønsted Acid Sites ◽  
Brönsted Acid ◽  
Ring Opening Reactions ◽  
Brönsted Acid Sites ◽  
Bronsted Acid Sites

The Cu(ii) coordination polymers with free –COOH groups as Brønsted acid sites show high activity and regioselectivity in catalyzing epoxide ring-opening reactions.

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>

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.

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