scholarly journals Hydrogen Bonding Networks Enable Brønsted Acid‐Catalyzed Carbonyl‐Olefin Metathesis

2022 ◽  
Author(s):  
Tuong Anh To ◽  
Chao Pei ◽  
Rene M. Koenigs ◽  
Thanh Vinh Nguyen
Keyword(s):  
Hydrogen Bonding ◽  
Olefin Metathesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Hydrogen Bonding Networks

scholarly journals Hydrogen Bonding Networks Enable Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis

2021 ◽  
Author(s):  
Tuong Anh To ◽  
Chao Pei ◽  
Rene Koenigs ◽  
Thanh Vinh Nguyen
Keyword(s):  
Hydrogen Bonding ◽  
Olefin Metathesis ◽  
Weak Interactions ◽  
Acid Catalyst ◽  
Spatial Arrangement ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Hydrogen Bonding Networks

Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen bonding networks, in order to enhance its catalytic activity to achieve a desired reaction outcome, is less explored in organic synthesis, despite being a commonly found phenomenon in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl-olefin metathesis reactions by hydrogen bonding-assisted Brønsted acid catalysis, using hexafluoroisopropanol (HFIP) solvent in combination with para-toluenesulfonic acid (pTSA). Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting pTSA Brønsted acid catalyst, but also insightful knowledge about the current limitations of the carbonyl-olefin metathesis reaction.

Brønsted Acid Catalyzed Domino 1,6-Addition/Intramolecular Cyclization­ Reactions: Diastereoselective Synthesis of Dihydro­coumarin Frameworks

Synthesis ◽  
2017 ◽  
Vol 50 (06) ◽  
pp. 1307-1314 ◽  
Author(s):  
Guang-Jian Mei ◽  
Zheng Cao ◽  
Gui-Xiang Zhou ◽  
Chun Ma ◽  
Kang Jiang
Keyword(s):  
Hydrogen Bonding ◽  
Crucial Role ◽  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diastereoselective Synthesis ◽  
Quinone Methides ◽  
Hydrogen Bonding Interactions ◽  
Brönsted Acid ◽  
Acid Catalyzed

An efficient domino 1,6-addition/intramolecular cyclization reaction between para-quinone methides (p-QMs) and azlactones under Brønsted acid catalysis was established. A series of highly functionalized dihydrocoumarins were constructed in good to excellent yields (up to 96%) with excellent diastereoselectivities (all >20:1 d.r.). In this process, the Brønsted acid plays a crucial role not only in activating the two substrates, but also in controlling the diastereoselectivity of the reaction via hydrogen-bonding interactions. In addition, this protocol demonstrates the great practicability of utilizing p-QMs in domino reactions.

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

Brønsted Acid-Catalyzed Friedel-Crafts-type Alkylation of Arenes with αAryl Diazoacetates

2021 ◽  
pp. 152751
Author(s):  
Wenming Chen ◽  
Guifang Chen ◽  
Biao Wang ◽  
Wei Wang ◽  
Wei Huang ◽  
...  
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed
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