Homogeneous metal-catalyzed exchange of aromatic compounds. Isotopic hydrogen labeling procedure

1967 ◽  
Vol 89 (17) ◽  
pp. 4546-4547 ◽  
Author(s):  
John L. Garnett ◽  
R. J. Hodges
Keyword(s):  
Aromatic Compounds ◽  
Isotopic Hydrogen ◽  
Metal Catalyzed

scholarly journals Recent Advances in the Synthesis of Isocoumarins and Polyaromatic Hydrocarbons for Photoactive Materials

INEOS OPEN ◽  
2021 ◽  
Vol 4 ◽  
Author(s):  
M. A. Arsenov ◽  
◽  
D. A. Loginov ◽  
Keyword(s):  
Aromatic Compounds ◽  
Heterocyclic Compounds ◽  
Polyaromatic Hydrocarbons ◽  
Reaction Products ◽  
Selective Activation ◽  
New Era ◽  
Aromatic Carbon ◽  
Ch Activation ◽  
Photoactive Materials ◽  
Metal Catalyzed

The discovery of transition metal-catalyzed selective activation of aromatic carbon–hydrogen bonds in 1993 has opened a new era in the synthesis of carbo- and heterocyclic compounds. This review covers the applications of oxidative annulations of aromatic compounds with alkynes involving CH activation for the synthesis of isocoumarins and polyaromatic hydrocarbons (PAHs). The limitations, advantages, and mechanical aspects of this approach as well as the current tendencies in the application of the reaction products for photoactive materials are discussed.

Transition metal catalyzed meta-C–H functionalization of aromatic compounds

2015 ◽  
Vol 13 (7) ◽  
pp. 1930-1941 ◽  
Author(s):  
Jiong Yang
Keyword(s):  
Transition Metal ◽  
Aromatic Compounds ◽  
Synthetic Methods ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This review summarizes synthetic methods for directing group guided, transition metal catalyzed meta-C–H functionalization of aromatic compounds.

scholarly journals Arenophile-Mediated Photochemical Dearomatization of Nonactivated Arenes

2020 ◽  
Vol 74 (7) ◽  
pp. 577-583 ◽  
Author(s):  
Mikiko Okumura ◽  
David Sarlah
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Visible Light ◽  
Bioactive Compounds ◽  
Aromatic Compounds ◽  
Ring Opening ◽  
Organic Molecules ◽  
Building Blocks ◽  
Metal Catalyzed

Aromatic compounds are one of the most abundant classes of organic molecules and find utility as precursors for alicyclic hydrocarbon building blocks. While many established dearomatization reactions are exceptionally powerful, dearomatization with concurrent introduction of functionality, i.e. dearomative functionalization, is still a largely underdeveloped field. This review aims to provide an overview of our recent efforts and progress in the development of dearomative functionalization of simple and nonactivated arenes using arenophile-arene cycloaddition platform. These cycloadducts, formed via a visible-light-mediated [4+2]-photocycloaddition, can be elaborated in situ through olefin chemistry or transition-metal-catalyzed ring-opening with carbon-, nitrogen-, and oxygen-based nucleophiles, providing access to diverse structures with functional and stereochemical complexity. Moreover, the dearomatized products are amenable to further elaborations, which effectively install other functionalities onto the resulting alicyclic carbocycles. The utility of the arenophile-mediated dearomatization methods are also highlighted by the facile syntheses of natural products and bioactive compounds through novel disconnections.

Migratory Insertion Strategies for Dearomatization

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4137-4146 ◽  
Author(s):  
Nicolas Zeidan ◽  
Mark Lautens
Keyword(s):  
Aromatic Compounds ◽  
Heck Reaction ◽  
Short Review ◽  
Stabilization Energy ◽  
Heck Reactions ◽  
Migratory Insertion ◽  
Resonance Stabilization ◽  
Metal Catalyzed ◽  
The Cost

Development of strategies for molecule functionalization by dearomatization has surged in the last two decades. The benefits of overcoming the resonance stabilization energy outweigh the cost; diverse compounds could be accessed in a short number of steps. One approach that has been of interest in recent years is the dearomatization of indoles and other (hetero)aromatic compounds by migratory insertion. The chiral σ-bond palladium intermediate could be reduced or trapped by a second functionalization. In this short review we will summarize the recently discovered reactions from our group and others in this field of metal-catalyzed dearomatizations by migratory insertion.1 Introduction2 Monofunctionalizations: Heck and Reductive Heck Reactions2.1 N-Tethered Heterocycles2.2 Non-N-tethered Heterocycles2.3 Non-heterocycles3 Dearomative Difunctionalizations: Interrupted Heck Reaction3.1 N-Tethered Heterocycles3.2 Non-N-tethered Heterocycles4 Conclusion

Dearomatization–Rearomatization Strategy for Palladium-Catalyzed C–N Cross-Coupling Reactions

Synlett ◽  
2020 ◽  
Author(s):  
Chao-Jun Li ◽  
Huiying Zeng ◽  
Yatao Lang
Keyword(s):  
Organic Chemistry ◽  
Aromatic Compounds ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Diphenyl Ethers ◽  
Palladium Catalyzed ◽  
History Of ◽  
Metal Catalyzed

AbstractSubstituted aromatic compounds play important roles in materials, biological agents, dyes, etc. Thus, the synthesis of substituted aromatic compounds has been a hot topic throughout the history of organic chemistry. Traditionally, the Friedel–Crafts reaction was a powerful tool for synthesizing substituted aromatic compounds. In recent decades, metal-catalyzed cross-coupling reactions were well developed via carbon–heteroatom bond cleavage, however, having difficulties towards some strong bonds, such as C(Ar)–OH. To overcome such challenges, newer strategies are needed. In this review, we summarize the recent efforts in the development of dearomatization–rearomatization strategy for cross-coupling reactions via C(Ar)–O bond cleavage.1 Introduction2 Dearomatization–Rearomatization Strategy for Cross-Coupling of Phenols3 Dearomatization–Rearomatization Strategy for Cross-Coupling of Biphenols4 Dearomatization–Rearomatization Strategy for Cross-Coupling of Diphenyl Ethers5 Dearomatization–Rearomatization Strategy for Cross-Coupling of Indoles6 Summary

Sign in / Sign up

Export Citation Format

Share Document