Palladium-catalyzed decarboxylative C3-acylation of benzofurans and benzothiophenes with α-oxocarboxylic acids via direct sp2 C–H bond activation

Tetrahedron ◽  
2015 ◽  
Vol 71 (8) ◽  
pp. 1269-1275 ◽  
Author(s):  
Wei-Jie Gong ◽  
De-Xian Liu ◽  
Fei-Long Li ◽  
Jun Gao ◽  
Hong-Xi Li ◽  
...  
Keyword(s):  
Bond Activation ◽  
Palladium Catalyzed ◽  
Oxocarboxylic Acids

ChemInform Abstract: Palladium-Catalyzed Decarboxylative C3-Acylation of Benzofurans and Benzothiophenes with α-Oxocarboxylic Acids via Direct sp2C-H Bond Activation.

ChemInform ◽  
2015 ◽  
Vol 46 (26) ◽  
pp. no-no
Author(s):  
Wei-Jie Gong ◽  
De-Xian Liu ◽  
Fei-Long Li ◽  
Jun Gao ◽  
Hong-Xi Li ◽  
...  
Keyword(s):  
Bond Activation ◽  
Palladium Catalyzed ◽  
Oxocarboxylic Acids

Theoretical and experimental studies of palladium-catalyzed site-selective C(sp3)−H bond functionalization enabled by transient ligands

2017 ◽  
Author(s):  
Haibo Ge ◽  
Lei Pan ◽  
Piaoping Tang ◽  
Ke Yang ◽  
Mian Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Theoretical Calculations ◽  
Experimental Studies ◽  
Bond Functionalization ◽  
Aliphatic Ketones ◽  
Site Selectivity ◽  
Mechanistic Investigation ◽  
Palladium Catalyzed ◽  
Metal Catalyzed ◽  
Site Selective

Transition metal-catalyzed selective C–H bond functionalization enabled by transient ligands has become an extremely attractive topic due to its economical and greener characteristics. However, catalytic pathways of this reaction process on unactivated sp<sup>3</sup> carbons of reactants have not been well studied yet. Herein, detailed mechanistic investigation on Pd-catalyzed C(sp<sup>3</sup>)–H bond activation with amino acids as transient ligands has been systematically conducted. The theoretical calculations showed that higher angle distortion of C(sp2)-H bond over C(sp3)-H bond and stronger nucleophilicity of benzylic anion over its aromatic counterpart, leading to higher reactivity of corresponding C(sp<sup>3</sup>)–H bonds; the angle strain of the directing rings of key intermediates determines the site-selectivity of aliphatic ketone substrates; replacement of glycine with β-alanine as the transient ligand can decrease the angle tension of the directing rings. Synthetic experiments have confirmed that β-alanine is indeed a more efficient transient ligand for arylation of β-secondary carbons of linear aliphatic ketones than its glycine counterpart.<br><br>

Palladium-Catalyzed C–C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides

2021 ◽  
Vol 86 (3) ◽  
pp. 2682-2695
Author(s):  
Tanmayee Nanda ◽  
Pragati Biswal ◽  
Bedadyuti Vedvyas Pati ◽  
Shyam Kumar Banjare ◽  
Ponneri Chandrababu Ravikumar
Keyword(s):  
Bond Activation ◽  
Unsaturated Esters ◽  
Palladium Catalyzed

α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles

2021 ◽  
Vol 23 (8) ◽  
pp. 2878-2883
Author(s):  
Liwei Zhou ◽  
Shujia Qiao ◽  
Fengru Zhou ◽  
Xinyu Xuchen ◽  
Guobo Deng ◽  
...  
Keyword(s):  
Palladium Catalyzed ◽  
Oxocarboxylic Acids

Palladium‐Catalyzed C‐C Bond Activation/Suzuki Reaction of Methylenecyclobutanes †

2021 ◽  
Author(s):  
Xiao‐Bing Chen ◽  
Li Li ◽  
Wan‐Chun Yang ◽  
Kun‐Long Song ◽  
Bin Wu ◽  
...  
Keyword(s):  
Bond Activation ◽  
Suzuki Reaction ◽  
Palladium Catalyzed

Palladium-catalyzed synthesis of aromatic acids from carbon monoxide and aromatic compounds via the aromatic CH bond activation

1990 ◽  
Vol 385 (2) ◽  
pp. 297-306 ◽  
Author(s):  
Tetsuro Jintoku ◽  
Yuzo Fujiwara ◽  
Itaru Kawata ◽  
Tomio Kawauchi ◽  
Hiroshi Taniguchi
Keyword(s):  
Carbon Monoxide ◽  
Aromatic Compounds ◽  
Bond Activation ◽  
Aromatic Acids ◽  
Palladium Catalyzed
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