Palladium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles via Enantioselective C–H Bond Functionalization

2012 ◽  
Vol 134 (17) ◽  
pp. 7305-7308 ◽  
Author(s):  
Ryo Shintani ◽  
Haruka Otomo ◽  
Kensuke Ota ◽  
Tamio Hayashi
Keyword(s):  
Asymmetric Synthesis ◽  
Bond Functionalization ◽  
Palladium Catalyzed

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>

Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of α-fluoro-β-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers

RSC Advances ◽  
2016 ◽  
Vol 6 (88) ◽  
pp. 85058-85062 ◽  
Author(s):  
Mayaka Maeno ◽  
Hiroya Kondo ◽  
Etsuko Tokunaga ◽  
Norio Shibata
Keyword(s):  
Alzheimer’S Disease ◽  
Alzheimer's Disease ◽  
Asymmetric Synthesis ◽  
Therapeutic Agent ◽  
The Self ◽  
Keto Ester ◽  
Catalytic Asymmetric Synthesis ◽  
Palladium Catalyzed ◽  
Catalytic Asymmetric ◽  
Decarboxylative Allylation

Catalytic asymmetric synthesis of fluorinated donepezil, a promising new therapeutic agent for Alzheimer's disease, was achieved.

Asymmetric Synthesis of β-Lactam via Palladium-Catalyzed Enantioselective Intramolecular C(sp3)–H Amidation

ACS Catalysis ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 114-120 ◽  
Author(s):  
Hua-Rong Tong ◽  
Wenrui Zheng ◽  
Xiaoyan Lv ◽  
Gang He ◽  
Peng Liu ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Palladium Catalyzed

Palladium-Catalyzed Asymmetric Synthesis of Axially Chiral Allenylsilanes and Their Application to SE2′ Chirality Transfer Reactions

2010 ◽  
Vol 12 (24) ◽  
pp. 5736-5739 ◽  
Author(s):  
Masamichi Ogasawara ◽  
Atsushi Okada ◽  
Velusamy Subbarayan ◽  
Sebastian Sörgel ◽  
Tamotsu Takahashi
Keyword(s):  
Asymmetric Synthesis ◽  
Transfer Reactions ◽  
Chirality Transfer ◽  
Axially Chiral ◽  
Palladium Catalyzed
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