Palladium-catalyzed Carbonylation of Polychlorinated Pyridines. A Simple Laboratory Approach to Metal Catalyzed Carbonylation Reactions

Heterocycles ◽  
2004 ◽  
Vol 63 (2) ◽  
pp. 411 ◽  
Author(s):  
John W. Hull, Jr. ◽  
Chen Wang
Keyword(s):  
Palladium Catalyzed ◽  
Metal 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>

scholarly journals Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 238-254
Author(s):  
Fulin Zhang ◽  
Luoting Xin ◽  
Saihu Liao ◽  
Xueliang Huang ◽  
Yinghua Yu
Keyword(s):  
Bond Distance ◽  
Short Review ◽  
Diazo Compounds ◽  
Bond Functionalization ◽  
Migratory Insertion ◽  
Intramolecular Reactions ◽  
Palladium Catalyzed ◽  
Direct Functionalization ◽  
Intermolecular Reactions ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed direct inert C–H bond functionalization has attracted much attention over the past decades. However, because of the high strain energy of the suspected palladacycle generated via C–H bond palladation, direct functionalization of a C–H bond less than a three-bond distance from a catalyst center is highly challenging. In this short review, we summarize the advances on palladium-catalyzed bridging C–H activation, in which an inert proximal C–H bond palladation is promoted by the elementary step of migratory insertion of an alkene, an alkyne or a metal carbene intermediate.1 Introduction2 Palladium-Catalyzed Alkene Bridging C–H Activation2.1 Intramolecular Reactions2.2 Intermolecular Reactions3 Palladium-Catalyzed Alkyne Bridging C–H Activation3.1 Intermolecular Reactions3.2 Intramolecular Reactions4 Palladium-Catalyzed Carbene Bridging C–H Activation5 Conclusion and Outlook

Transition metal-catalyzed reactions in heterocyclic chemistry

2002 ◽  
Vol 74 (8) ◽  
pp. 1327-1337 ◽  
Author(s):  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Heterocyclic Chemistry ◽  
Substitution Reactions ◽  
Multiple Bonds ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

The palladium-catalyzed substitution reactions forming carbon­carbon and carbon­element bonds, as well as nickel-catalyzed addition of E­H and E­E' bonds across multiple bonds, are considered in their application to the chemistry of heterocyclic compounds.

Recent Advances in Piperazine Synthesis

Synthesis ◽  
2017 ◽  
Vol 49 (12) ◽  
pp. 2589-2604 ◽  
Author(s):  
Kristen Gettys ◽  
Zhishi Ye ◽  
Mingji Dai
Keyword(s):  
Transition Metal ◽  
Small Molecule ◽  
Ring System ◽  
Reductive Cyclization ◽  
The Third ◽  
Methods Development ◽  
Recent Advances ◽  
Borrowing Hydrogen ◽  
Palladium Catalyzed ◽  
Metal Catalyzed

Piperazine ranks as the third most common N-heterocycle appearing in small-molecule pharmaceuticals. This review highlights recent advances in methods development for the construction of the piperazine­ ring system with particular emphasis on preparing carbon-substituted piperazines.1 Introduction2 Reduction of (Di)ketopiperazine3 N-Alkylation4 Transition-Metal-Catalyzed/Mediated Piperazine Synthesis4.1 The SnAP and SLAP Methods4.2 Palladium-Catalyzed Cyclization4.3 Gold-Catalyzed Cyclization4.4 Other Metal-Catalyzed/Mediated Cyclization4.5 Borrowing Hydrogen Strategy4.6 Imine Reductive Cyclization5 Reduction of Pyrazines6 Miscellaneous7 Conclusion

Regiocontrolled palladium-catalyzed and copper-mediated C–H bond functionalization of protectedl-histidine

2014 ◽  
Vol 12 (23) ◽  
pp. 3792-3796 ◽  
Author(s):  
Amit Mahindra ◽  
Rahul Jain
Keyword(s):  
Transition Metal ◽  
Aryl Halides ◽  
Bond Functionalization ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Coupling Partner

Regiocontrolled transition-metal-catalyzed C–H bond arylation of protectedl-histidine with aryl halides as the coupling partner is reported.

Transition-Metal-Catalyzed Cross-Coupling with Non-Diazo Carbene Precursors

Synlett ◽  
2018 ◽  
Vol 30 (05) ◽  
pp. 542-551 ◽  
Author(s):  
Jianbo Wang ◽  
Kang Wang
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Diazo Compounds ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed ◽  
Fischer Carbenes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Transition-metal-catalyzed cross-coupling reactions through metal carbene migratory insertion have emerged as powerful methodology for carbon–carbon bond constructions. Typically, diazo compounds (or in situ generated diazo compounds from N-tosylhydrazones) have been employed as the metal carbene precursors for this type of cross-coupling reactions. Recently, cross-coupling reactions employing non-diazo carbene precursors, such as conjugated ene-yne-ketones, allenyl ketones, alkynes, cyclopropenes, and Cr(0) Fischer carbenes, have been developed. This account will summarize our efforts in the development of transition-metal-catalyzed cross-coupling reactions with these non-diazo carbene precursors.1 Introduction2 Cross-Coupling with Ene-yne-ketones, Allenyl Ketones, and Alkynes3 Cross-Coupling Involving Ring-Opening of Cyclopropenes4 Palladium-Catalyzed Cross-Coupling with Chromium(0) Fischer Carbenes5 Conclusion

Sign in / Sign up

Export Citation Format

Share Document