Introverted Brønsted acid cavitands for selective conjugate addition reactions

2021 ◽  
pp. 1-13
Author(s):  
Yasuhiro Matsumoto ◽  
Yuta Taguchi ◽  
Naruhiro Yoshida ◽  
Shugo Tokai ◽  
Tomoyuki Maruyama ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
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>

scholarly journals Brønsted acid-catalysed conjugate addition of photochemically generated α-amino radicals to alkenylpyridines

2016 ◽  
Vol 52 (17) ◽  
pp. 3520-3523 ◽  
Author(s):  
Hamish B. Hepburn ◽  
Paolo Melchiorre
Keyword(s):  
Conjugate Addition ◽  
Bronsted Acid ◽  
Photoredox Catalysis ◽  
Brønsted Acid ◽  
Brönsted Acid

The conjugate addition of α-amino radicals to alkenylpyridines is accomplished by the synergistic merger of Brønsted acid and photoredox catalysis.

Synthesis of Pyrrolo[1,2-a]indoles via (3+2)-Annulations of (Aza)-para-Quinone Methides with Indoles

Synthesis ◽  
2020 ◽  
Vol 52 (23) ◽  
pp. 3640-3649 ◽  
Author(s):  
Xiang-Zhi Zhang ◽  
Bao Qiong Li ◽  
Zong-Wang Qiu ◽  
Gui-Hua Wen ◽  
Ai-Jun Ma ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Quinone Methides ◽  
Propargylic Alcohols ◽  
Brönsted Acid

An efficient and straightforward Brønsted acid mediated (3+2)-annulation of (aza)-para-quinone methides, generated in situ from propargylic alcohols and indoles, has been developed involving 1,8-conjugate addition/5-endo annulation cascade. This protocol affords a mild and effective method for the construction of synthetically important and structurally interesting functionalized pyrrolo[1,2-a]indoles.

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