Palladium-Catalyzed Direct Acylation of Ketoximes and Aldoximes from the Alcohol Oxidation Level through C-H Bond Activation

2013 ◽  
Vol 2013 (29) ◽  
pp. 6656-6665 ◽  
Author(s):  
Satyasheel Sharma ◽  
Minyoung Kim ◽  
Jihye Park ◽  
Mirim Kim ◽  
Jong Hwan Kwak ◽  
...  
ChemInform ◽  
2014 ◽  
Vol 45 (11) ◽  
pp. no-no
Author(s):  
Satyasheel Sharma ◽  
Minyoung Kim ◽  
Jihye Park ◽  
Mirim Kim ◽  
Jong Hwan Kwak ◽  
...  

2013 ◽  
Vol 11 (17) ◽  
pp. 2766 ◽  
Author(s):  
Jihye Park ◽  
Aejin Kim ◽  
Satyasheel Sharma ◽  
Minyoung Kim ◽  
Eonjeong Park ◽  
...  

2017 ◽  
Author(s):  
Haibo Ge ◽  
Lei Pan ◽  
Piaoping Tang ◽  
Ke Yang ◽  
Mian Wang ◽  
...  

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>


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

Author(s):  
Xiao‐Bing Chen ◽  
Li Li ◽  
Wan‐Chun Yang ◽  
Kun‐Long Song ◽  
Bin Wu ◽  
...  

1990 ◽  
Vol 385 (2) ◽  
pp. 297-306 ◽  
Author(s):  
Tetsuro Jintoku ◽  
Yuzo Fujiwara ◽  
Itaru Kawata ◽  
Tomio Kawauchi ◽  
Hiroshi Taniguchi

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