Pd-Catalyzed [3+2] cycloaddition of ketoimines with alkynes via directed sp3 C–H bond activation

2014 ◽  
Vol 50 (73) ◽  
pp. 10699-10702 ◽  
Author(s):  
Ying Xie ◽  
Tengfei Chen ◽  
Shaomin Fu ◽  
Xing-Shu Li ◽  
Yuanfu Deng ◽  
...  
Keyword(s):  
Bond Activation ◽  
Efficient Access ◽  
Palladium Catalyzed

The palladium-catalyzed oxidative [3+2] cycloaddition of ketoimines with alkynes provided an efficient access to multisubstituted pyrroles via Csp3–H activation.

Synthesis of Phenanthridinones by Palladium-Catalyzed Cyclization of N-Aryl-2-aminopyridines with 2-Iodobenzoic Acids in Water

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 280-284
Author(s):  
Xiaojuan Ding ◽  
Lei Zhang ◽  
Yiyang Mao ◽  
Binsen Rong ◽  
Ning Zhu ◽  
...  
Keyword(s):  
Bond Activation ◽  
Efficient Access ◽  
Palladium Catalyzed

The first Pd-catalyzed cyclization of N-aryl-2-aminopyridines with 2-iodobenzoic acids for the synthesis of phenanthridinones through C–H bond activation under very low catalyst loadings (down to 0.1 mol% Pd) in water is reported. This protocol features a broad substrate scope and provides easy efficient access to various phenanthridinones.

NHC ligand-powered palladium-catalyzed carbonylative C–S bond cleavage of vinyl sulfides: efficient access to tert-butyl arylacrylates

2020 ◽  
Vol 18 (48) ◽  
pp. 9796-9799
Author(s):  
Jian-Xing Xu ◽  
Fengqian Zhao ◽  
Xiao-Feng Wu
Keyword(s):  
Bond Activation ◽  
Bond Cleavage ◽  
Tert Butyl ◽  
Efficient Access ◽  
Vinyl Sulfides ◽  
Palladium Catalyzed

A palladium-catalyzed carbonylative C–S bond activation of divinyl sulfides to synthesize various tert-(E)-butyl arylacrylates under 1 bar of CO has been developed. A series of tert-(E)-butyl acrylates were obtained in moderate to good yields.

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>

Sequential C-Selective Difluoromethylation/Pd-Catalyzed Decarboxylative Protonation: An Efficient Access to Tertiary Difluoromethylated Scaffolds

2019 ◽  
Author(s):  
Nicolas Duchemin ◽  
Roberto Buccafusca ◽  
Marc Daumas ◽  
Vincent Ferey ◽  
Stellios Arseniyadis
Keyword(s):  
Drug Development ◽  
Late Stage ◽  
Efficient Access ◽  
Palladium Catalyzed ◽  
General Method

We report here a general method that allows a highly straightforward access to tertiary difluoromethylated compounds. The strategy relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and an unprecedented palladium-catalyzed decarboxylative protonation. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.<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

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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