C(sp3)–C(sp3) bond formation via copper/Brønsted acid co-catalyzed C(sp3)–H bond oxidative cross-dehydrogenative-coupling (CDC) of azaarenes

2014 ◽  
Vol 16 (5) ◽  
pp. 2428 ◽  
Author(s):  
Fang-Fang Wang ◽  
Cui-Ping Luo ◽  
Guojun Deng ◽  
Luo Yang
Keyword(s):  
Bond Formation ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Dehydrogenative Coupling ◽  
Brönsted Acid

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>

Hydrogen Bond Formation of Brønsted Acid Sites in Zeolites

2020 ◽  
Vol 32 (4) ◽  
pp. 1564-1574 ◽  
Author(s):  
Christian Schroeder ◽  
Vassilios Siozios ◽  
Christian Mück-Lichtenfeld ◽  
Michael Hunger ◽  
Michael Ryan Hansen ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Bond Formation ◽  
Acid Sites ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brønsted Acid Sites ◽  
Hydrogen Bond Formation ◽  
Brönsted Acid ◽  
Brönsted Acid Sites ◽  
Bronsted Acid Sites

Metal free carboamination of internal alkynes – an easy access to polysubstituted quinolines

2016 ◽  
Vol 52 (33) ◽  
pp. 5761-5764 ◽  
Author(s):  
T. Stopka ◽  
M. Niggemann
Keyword(s):  
Bond Formation ◽  
Acid Catalyst ◽  
Easy Access ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Metal Free ◽  
Brönsted Acid ◽  
Brønsted Acid Catalyst ◽  
Internal Alkynes ◽  
Brönsted Acid Catalyst

A synergistic Brønsted acid catalyst was used to intermolecularly generate vinyl cations for a C–C bond formation – Schmidt rearrangement – sequence.

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