scholarly journals Versatile and Ligand-Free Copper-Catalyzed α-Arylations of Aromatic Ketones Using Diaryliodonium Salts

2021 ◽  
Author(s):  
Maxime Bouquin ◽  
Florian Jaroschik ◽  
Marc Taillefer
Keyword(s):  
Functional Group ◽  
Catalyst Loading ◽  
Synthetic Methodology ◽  
Enol Ethers ◽  
Aromatic Ketones ◽  
Silyl Enol Ethers ◽  
Diaryliodonium Salts ◽  
Ligand Free ◽  
Low Catalyst Loading

A ligand and base free copper catalyzed synthetic methodology for the efficient alpha-arylation of aromatic ketones has been developed. The reaction of the ketone-derived silyl enol ethers with diaryliodonium salts led to the intermolecular C-C coupling displaying high functional group tolerance with a low catalyst loading.<br>

scholarly journals Versatile and Ligand-Free Copper-Catalyzed α-Arylations of Aromatic Ketones Using Diaryliodonium Salts

2021 ◽  
Author(s):  
Maxime Bouquin ◽  
Florian Jaroschik ◽  
Marc Taillefer
Keyword(s):  
Functional Group ◽  
Catalyst Loading ◽  
Synthetic Methodology ◽  
Enol Ethers ◽  
Aromatic Ketones ◽  
Silyl Enol Ethers ◽  
Diaryliodonium Salts ◽  
Ligand Free ◽  
Low Catalyst Loading

A ligand and base free copper catalyzed synthetic methodology for the efficient alpha-arylation of aromatic ketones has been developed. The reaction of the ketone-derived silyl enol ethers with diaryliodonium salts led to the intermolecular C-C coupling displaying high functional group tolerance with a low catalyst loading.<br>

Palladium-catalyzed Sonogashira coupling of amides: access to ynones via C–N bond cleavage

2016 ◽  
Vol 52 (81) ◽  
pp. 12076-12079 ◽  
Author(s):  
Ming Cui ◽  
Hongxiang Wu ◽  
Junsheng Jian ◽  
Hui Wang ◽  
Chao Liu ◽  
...  
Keyword(s):  
Functional Group ◽  
Bond Cleavage ◽  
Catalyst Loading ◽  
Sonogashira Coupling ◽  
Broad Array ◽  
Palladium Catalyzed ◽  
Low Catalyst Loading

The first palladium-catalyzed Sonogashira coupling of amides has been developed, which proceeds via a selective cleavage of the N-acylsaccharin C–N bond. The protocol is mild, highly functional group tolerant and can be efficiently employed in the synthesis of a broad array of ynones in 48–98% yields under low catalyst loading and Cu-free conditions.

scholarly journals Direct Access to Mono-Protected Homoallylic 1,2-Diols via Dual Chromium/ Photoredox Catalysis

2020 ◽  
Author(s):  
Felix Schäfers ◽  
Linda Quach ◽  
J. Luca Schwarz ◽  
Mar Saladrigas ◽  
Constantin G. Daniliuc ◽  
...  
Keyword(s):  
Functional Group ◽  
Protecting Groups ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Efficient Synthesis ◽  
Enol Ethers ◽  
Silyl Enol Ethers

<p>A dual catalytic strategy enables the efficient synthesis of mono-protected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super)stoichiometric use of prefunctionalized metal-allyl species. A variety of silyl- and alkyl-based protecting groups is shown and functional group tolerance, chemoselectivity and scalability are highlighted. </p>

scholarly journals Copper-catalyzed aerobic decarboxylative coupling between cyclic α-amino acids and diverse C–H nucleophiles with low catalyst loading

RSC Advances ◽  
2018 ◽  
Vol 8 (29) ◽  
pp. 16202-16206 ◽  
Author(s):  
Jing Guo ◽  
Ying Xie ◽  
Qiao-Lei Wu ◽  
Wen-Tian Zeng ◽  
Albert S. C. Chan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Cross Coupling ◽  
Catalyst Loading ◽  
Ligand Free ◽  
Decarboxylative Coupling ◽  
Low Catalyst Loading

An aerobic decarboxylative cross-coupling of α-amino acids was realized using 1 mol% Cu2(OH)2CO3 catalyst under ligand free conditions.

scholarly journals Direct Access to Mono-Protected Homoallylic 1,2-Diols via Dual Chromium/ Photoredox Catalysis

2020 ◽  
Author(s):  
Felix Schäfers ◽  
Linda Quach ◽  
J. Luca Schwarz ◽  
Mar Saladrigas ◽  
Constantin G. Daniliuc ◽  
...  
Keyword(s):  
Functional Group ◽  
Protecting Groups ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Efficient Synthesis ◽  
Enol Ethers ◽  
Silyl Enol Ethers

<p>A dual catalytic strategy enables the efficient synthesis of mono-protected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super)stoichiometric use of prefunctionalized metal-allyl species. A variety of silyl- and alkyl-based protecting groups is shown and functional group tolerance, chemoselectivity and scalability are highlighted. </p>

scholarly journals Direct Access to Mono-Protected Homoallylic 1,2-Diols via Dual Chromium/ Photoredox Catalysis

2020 ◽  
Author(s):  
Felix Schäfers ◽  
Linda Quach ◽  
J. Luca Schwarz ◽  
Mar Saladrigas ◽  
Constantin G. Daniliuc ◽  
...  
Keyword(s):  
Functional Group ◽  
Protecting Groups ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Efficient Synthesis ◽  
Enol Ethers ◽  
Silyl Enol Ethers

<p>A dual catalytic strategy enables the efficient synthesis of mono-protected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super)stoichiometric use of prefunctionalized metal-allyl species. A variety of silyl- and alkyl-based protecting groups is shown and functional group tolerance, chemoselectivity and scalability are highlighted. </p>

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