A Direct Palladium-Catalyzed Route for the Synthesis of Benzo[a]carbazoles through Sequential C-C Bond Formation and C-H Bond Functionalization

2011 ◽  
Vol 2012 (2) ◽  
pp. 256-259 ◽  
Author(s):  
Ebrahim Kianmehr ◽  
Mohammad Ghanbari
Keyword(s):  
Bond Formation ◽  
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>

Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis

2021 ◽  
Author(s):  
K. R. Holman ◽  
A. M. Stanko ◽  
S. E. Reisman
Keyword(s):  
Natural Product ◽  
Bond Formation ◽  
Natural Product Synthesis ◽  
Cascade Cyclizations ◽  
Palladium Catalyzed ◽  
Multiple Rings

This tutorial review highlights the use of palladium-catalyzed cascade cyclizations in natural product synthesis, focusing on cascades that construct multiple rings and form both C–C and C–X (X = O, N) bonds in a single synthetic operation.

A Valuable Synthesis of Pyrrolo[1,2-a]quinoxalines, Indolo[1,2-a]quinoxalines and their Aza-Analogues by Palladium-Catalyzed Intramolecular Carbon-Nitrogen Bond Formation

Synthesis ◽  
2005 ◽  
Vol 2005 (17) ◽  
pp. 2881-2886 ◽  
Author(s):  
Egle M. Beccalli ◽  
Giorgio Abbiati ◽  
Gianluigi Broggini ◽  
Giuseppe Paladino ◽  
Elisabetta Rossi
Keyword(s):  
Bond Formation ◽  
Palladium Catalyzed ◽  
Nitrogen Bond
Sign in / Sign up

Export Citation Format

Share Document