The NHCs-mediated cross-coupling of aromatic aldehydes with benzyl halides: synthesis of α-aryl ketones

2010 ◽  
Vol 51 (27) ◽  
pp. 3571-3574 ◽  
Author(s):  
Lu Lin ◽  
Yi Li ◽  
Wenting Du ◽  
Wei-Ping Deng
Keyword(s):  
Cross Coupling ◽  
Aromatic Aldehydes ◽  
Aryl Ketones ◽  
Benzyl Halides

Nickel N-heterocyclic carbene-catalyzed cross-coupling reaction of aryl aldehydes with organozinc reagents to produce aryl ketones

2015 ◽  
Vol 5 (9) ◽  
pp. 4341-4345 ◽  
Author(s):  
Cheng Jin ◽  
Lijun Gu ◽  
Minglong Yuan
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Aromatic Aldehydes ◽  
Aryl Aldehydes ◽  
Cross Coupling Reaction ◽  
Aryl Ketones ◽  
Organozinc Reagents ◽  
Synthetic Utilization

The transformation of aromatic aldehydes into aryl ketones by nickel-catalyzed cross-coupling has been developed. This transformation represents an efficient and attractive synthetic utilization of organozinc reagents.

The Merger of CF3SO2Na and Palladium Catalysis to Enable Decarboxylative Cross-Coupling for the Synthesis of Aromatic Ketones under Room Temperature

2021 ◽  
Author(s):  
Pan Xie ◽  
Cheng Xue ◽  
Cancan Wang ◽  
Dongdong Du ◽  
Sanshan Shi
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Palladium Catalysis ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aromatic Ketones ◽  
Aryl Ketones ◽  
Oxocarboxylic Acids

A CF3SO2Na/Pd(OAc)2 co-catalyzed strategy is developed to produce aryl ketones via visible-light-induced decarboxylative cross-coupling of α-oxocarboxylic acids and aryl boronic acids. This process was perfomed under air at room temperature,...

Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates

2021 ◽  
Author(s):  
Tingting Yan ◽  
Kaki Raveendra Babu ◽  
Yong Wu ◽  
Yang Li ◽  
Yuhai Tang ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Benzyl Halides

Copper-catalyzed sp3-sp3 cross-coupling of turbo grignards with benzyl halides

2021 ◽  
pp. 153516
Author(s):  
Greg Petruncio ◽  
Synah Elahi-Mohassel ◽  
Michael Girgis ◽  
Mikell Paige
Keyword(s):  
Cross Coupling ◽  
Benzyl Halides

scholarly journals DABCO-promoted photocatalytic C–H functionalization of aldehydes

2021 ◽  
Vol 17 ◽  
pp. 2959-2967
Author(s):  
Bruno Maia da Silva Santos ◽  
Mariana dos Santos Dupim ◽  
Cauê Paula de Souza ◽  
Thiago Messias Cardozo ◽  
Fernanda Gadini Finelli
Keyword(s):  
Hydrogen Atom ◽  
Cross Coupling ◽  
Hydrogen Atom Transfer ◽  
Direct Application ◽  
Atom Transfer ◽  
Organic Base ◽  
Aryl Bromides ◽  
Computational Calculations ◽  
Acyl Radicals ◽  
Aryl Ketones

Herein we present a direct application of DABCO, an inexpensive and broadly accessible organic base, as a hydrogen atom transfer (HAT) abstractor in a photocatalytic strategy for aldehyde C–H activation. The acyl radicals generated in this step were arylated with aryl bromides through a well stablished nickel cross-coupling methodology, leading to a variety of interesting aryl ketones in good yields. We also performed computational calculations to shine light in the HAT step energetics and determined an optimized geometry for the transition state, showing that the hydrogen atom transfer between aldehydes and DABCO is a mildly endergonic, yet sufficiently fast step. The same calculations were performed with quinuclidine, for comparison of both catalysts and the differences are discussed.

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