Palladium-catalyzed [2+1+1] annulation of norbornenes with (z)-bromostyrenes: synthesis of bismethylenecyclobutanes via twofold C(sp2)–H bond activation

2014 ◽  
Vol 50 (99) ◽  
pp. 15726-15729 ◽  
Author(s):  
Jiangang Mao ◽  
Weiliang Bao
Keyword(s):  
Bond Activation ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Palladium Catalyzed

A Pd(0)-catalyzed domino bismethylenecyclobutanation reaction was established. The [2+1+1] cycloaddition involves twofold C(sp2)–H bond activation and formation of three carbon–carbon bonds.

scholarly journals Direct activation of relatively unstrained carbon–carbon bonds in homogeneous systems

2014 ◽  
Vol 1 (5) ◽  
pp. 567-581 ◽  
Author(s):  
Alpay Dermenci ◽  
Jotham W. Coe ◽  
Guangbin Dong
Keyword(s):  
Bond Activation ◽  
State Of The Art ◽  
Carbon Bond ◽  
Homogeneous Systems ◽  
Direct Activation ◽  
Carbon Carbon Bond ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Art Methods

This review highlights the frontier of carbon–carbon bond activation and discusses state-of-the-art methods for activating relatively unstrained bonds in homogeneous systems.

scholarly journals Silacyclization through Palladium-Catalyzed Intermolecular Silicon-Based C(sp2)−C(sp3) Cross-Coupling

2021 ◽  
Author(s):  
Ying Qin ◽  
Lianghui Li ◽  
Jin-Yuan Liang ◽  
Kailong Li ◽  
Dongbing Zhao
Keyword(s):  
Cross Coupling ◽  
Ring Expansion ◽  
Expansion Strategy ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Palladium Catalyzed ◽  
Silicon Based

Silicon-based cross-coupling has been recognized as one of the most reliable alternatives for constructing carbon−carbon bonds. However, the employment of such reaction as an efficient ring expansion strategy for silacycle...

Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions

2015 ◽  
Vol 51 (85) ◽  
pp. 15522-15525 ◽  
Author(s):  
A. L. Stein ◽  
F. N. Bilheri ◽  
G. Zeni
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Palladium Catalyzed

A powerful tool for constructing new carbon–carbon bonds via palladium-catalyzed cross-coupling reactions of unsaturated organoselenides is described.

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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