Transition metal-catalyzed carbocyclization of nitrogen and oxygen-tethered 1,n-enynes and diynes: synthesis of five or six-membered heterocyclic compounds

2012 ◽  
Vol 48 (83) ◽  
pp. 10271 ◽  
Author(s):  
Di-Han Zhang ◽  
Zhen Zhang ◽  
Min Shi
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

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 the Transition Metal Catalyzed Addition of Carboxylic Acids to Alkynes

2021 ◽  
Vol 25 ◽  
Author(s):  
Victorio Cadierno
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Recent Advances ◽  
Enol Esters ◽  
Cascade Processes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: Recent advances in the metal-catalyzed hydrofunctionalization of alkynes with carboxylic acids are comprehensively reviewed. Both inter- and intramolecular processes, leading respectively to enol esters and lactones, are discussed, as well as the involvement of these transformations in the synthesis of natural products and biologically active molecules, and the assembly of elaborated heterocyclic compounds though cascade processes. Literature published since 2011 is covered.

scholarly journals Opportunities and challenges for direct C–H functionalization of piperazines

2016 ◽  
Vol 12 ◽  
pp. 702-715 ◽  
Author(s):  
Zhishi Ye ◽  
Kristen E Gettys ◽  
Mingji Dai
Keyword(s):  
Transition Metal ◽  
Small Molecule ◽  
Heterocyclic Compounds ◽  
Structural Diversity ◽  
Synthetic Methods ◽  
Photoredox Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Nitrogen Heterocyclic

Piperazine ranks within the top three most utilized N-heterocyclic moieties in FDA-approved small-molecule pharmaceuticals. Herein we summarize the current synthetic methods available to perform C–H functionalization on piperazines in order to lend structural diversity to this privileged drug scaffold. Multiple approaches such as those involving α-lithiation trapping, transition-metal-catalyzed α-C–H functionalizations, and photoredox catalysis are discussed. We also highlight the difficulties experienced when successful methods for α-C–H functionalization of acyclic amines and saturated mono-nitrogen heterocyclic compounds (such as piperidines and pyrrolidines) were applied to piperazine substrates.

Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3818-3836
Author(s):  
Jin-Heng Li ◽  
De-Lie An ◽  
Jing-Hao Qin
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Cycloaddition Reactions ◽  
Structural Motifs ◽  
Recent Advances ◽  
Wide Range ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner with an emphasis on scope and limitations and with a discussion of the mechanisms.1 Introduction2 Intermolecular Cycloaddition To Construct Azepine Derivatives2.1 [5+2] Cycloaddition2.2 [3+2+2] Cycloaddition2.3 [3+2]/[5+2] Cycloaddition3 Intermolecular [4+2] Cycloaddition To Construct Isoquinolines or Isocoumarins4 Intermolecular [3+2] Cycloaddition To Construct Spirohetero­cyclic Compounds, Indoles, Furans, and Pyrroles5 Summary and Outlook

Chelation-assisted transition metal-catalysed C–H chalcogenylations

2020 ◽  
Vol 7 (8) ◽  
pp. 1022-1060 ◽  
Author(s):  
Wenbo Ma ◽  
Nikolaos Kaplaneris ◽  
Xinyue Fang ◽  
Linghui Gu ◽  
Ruhuai Mei ◽  
...  
Keyword(s):  
Transition Metal ◽  
Recent Advances ◽  
Site Selectivity ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This review summarizes recent advances in C–S and C–Se formations via transition metal-catalyzed C–H functionalization utilizing directing groups to control the site-selectivity.

Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

2020 ◽  
Vol 24 (3) ◽  
pp. 231-264 ◽  
Author(s):  
Kevin H. Shaughnessy
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Wide Range ◽  
Sterically Demanding ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

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