Cooperative Photoinduced/Brønsted Acid Catalyzed Cycloaddition of Transient Thioaldehydes and ortho-Quinone Methides toward a Synthesis of Benzo[e][1,3]oxathiines

2021 ◽  
Author(s):  
Florian Sachse ◽  
Christoph Schneider
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Quinone Methides ◽  
Brönsted Acid ◽  
Acid Catalyzed

Efficient Synthesis of Chromenes from Vinyl o-Quinone Methides via a Brønsted Acid Catalyzed Electrocyclization Process

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2416-2422 ◽  
Author(s):  
Man-Su Tu ◽  
Guang-Jian Mei ◽  
Feng Shi ◽  
Si-Jia Liu ◽  
Xiao-Li Jiang ◽  
...  
Keyword(s):  
Efficient Method ◽  
Research Area ◽  
Environmentally Benign ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Efficient Synthesis ◽  
Quinone Methides ◽  
Efficient Approach ◽  
Brönsted Acid ◽  
Acid Catalyzed

An efficient approach for the synthesis of chromene derivatives from vinyl o-quinone methides was established via a Brønsted acid catalyzed electrocyclization. By using this methodology, a series of structurally diversified chromenes was synthesized in a highly atom-economic and environmentally benign manner with generally good to excellent yields (up to 98% yield). This reaction will not only provide an efficient method for the construction of chromene scaffolds, but also enrich the research area of o-quinone methides.

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.

scholarly journals Chiral Brønsted acid-catalyzed Friedel–Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes

2015 ◽  
Vol 51 (8) ◽  
pp. 1461-1464 ◽  
Author(s):  
Satyajit Saha ◽  
Santosh Kumar Alamsetti ◽  
Christoph Schneider
Keyword(s):  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Quinone Methides ◽  
Reaction Conditions ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid ◽  
Hydrogen Bonded

Hydrogen-bonded, in situ-generated ortho-quinone methides undergo highly enantioselective Friedel–Crafts reactions with indoles and naphthols under mild reaction conditions.

Brønsted acid catalyzed radical addition to quinone methides

2021 ◽  
Author(s):  
Shiv Shankar Patel ◽  
Dileep Kumar ◽  
Chandra Bhushan Tripathi
Keyword(s):  
Alkyl Radical ◽  
Acid Catalysis ◽  
Radical Addition ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Quinone Methides ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Radical Generation

A fundamental quest for alkyl radical generation under mild conditions through photoinduced Brønsted acid catalysis is addressed.

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