Direct Arylation of Heterocycles: The Performances of Ferrocene-Based Polyphosphane Ligands in Palladium-Catalyzed CH Bond Activation

ChemCatChem ◽  
2010 ◽  
Vol 2 (3) ◽  
pp. 296-305 ◽  
Author(s):  
Julien Roger ◽  
Sophal Mom ◽  
Matthieu Beaupérin ◽  
Sylviane Royer ◽  
Philippe Meunier ◽  
...  
Keyword(s):  
Bond Activation ◽  
Direct Arylation ◽  
Palladium Catalyzed

Palladium-Catalyzed Intramolecular Direct Arylation of 2-Bromo-diaryl Sulfoxides via C–H Bond Activation

2013 ◽  
Vol 15 (10) ◽  
pp. 2490-2493 ◽  
Author(s):  
Thomas Wesch ◽  
Anaïs Berthelot-Bréhier ◽  
Frédéric R. Leroux ◽  
Françoise Colobert
Keyword(s):  
Bond Activation ◽  
Direct Arylation ◽  
Palladium Catalyzed

scholarly journals Palladium‐Catalyzed Direct Arylation of Azulene Based on Regioselective C−H Bond Activation

2016 ◽  
Vol 5 (5) ◽  
pp. 629-635 ◽  
Author(s):  
Masahito Murai ◽  
Mayu Yanagawa ◽  
Masahiro Nakamura ◽  
Kazuhiko Takai
Keyword(s):  
Bond Activation ◽  
Direct Arylation ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Direct Arylation of Azulene Based on Regioselective C-H Bond Activation.

ChemInform ◽  
2016 ◽  
Vol 47 (39) ◽  
Author(s):  
Masahito Murai ◽  
Mayu Yanagawa ◽  
Masahiro Nakamura ◽  
Kazuhiko Takai
Keyword(s):  
Bond Activation ◽  
Direct Arylation ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Intramolecular Direct Arylation of 2-Bromo-diaryl Sulfoxides via C-H Bond Activation.

ChemInform ◽  
2013 ◽  
Vol 44 (36) ◽  
pp. no-no
Author(s):  
Thomas Wesch ◽  
Anais Berthelot-Brehier ◽  
Frederic R. Leroux ◽  
Francoise Colobert
Keyword(s):  
Bond Activation ◽  
Direct Arylation ◽  
Palladium Catalyzed

ChemInform Abstract: Direct Arylation of Dithienylperfluorocyclopentenes via Palladium-Catalyzed C-H Bond Activation: A Simpler Access to Photoswitches.

ChemInform ◽  
2012 ◽  
Vol 43 (40) ◽  
pp. no-no
Author(s):  
Kassem Beydoun ◽  
Julien Boixel ◽  
Veronique Guerchais ◽  
Henri Doucet
Keyword(s):  
Bond Activation ◽  
Direct Arylation ◽  
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>

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