The Transient Directing Group Strategy: A New Trend in Transition-Metal-Catalyzed C–H Bond Functionalization

Synthesis ◽  
2017 ◽  
Vol 49 (21) ◽  
pp. 4808-4826 ◽  
Author(s):  
Tatiana Besset ◽  
Qun Zhao ◽  
Thomas Poisson ◽  
Xavier Pannecoucke
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Short Review ◽  
Point Of View ◽  
Bond Functionalization ◽  
Carbonyl Derivatives ◽  
Direct Functionalization ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

In recent years, the C–H bond activation field has known very fast expansion offering valuable synthetic tools. Consequently, the quest for new approaches to afford atom- and step-economical processes has driven the scientific community to imagine original strategies. In this context, the direct functionalization of substrates by a transition-metal-catalyzed C–H bond activation using a transient directing group has emerged as a promising approach. This short review focuses on the major progress made in this field to provide to the reader an overview of the recent advances.1 Introduction2 From a Historical Point of View3 Functionalization of Carbonyl Derivatives4 Functionalization of Amines Derivatives5 Summary and Outlook

scholarly journals Advances in the Synthesis of Fluorinated Scaffolds by Transition Metal-Catalyzed C–H Bond Activation

2020 ◽  
Vol 74 (11) ◽  
pp. 871-877
Author(s):  
Sara Mazeh ◽  
Maria Ivana Lapuh ◽  
Tatiana Besset
Keyword(s):  
Transition Metal ◽  
Fluorine Atom ◽  
Bond Activation ◽  
Value Added ◽  
Bond Functionalization ◽  
Present Account ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Thanks to the unique features of the fluorine atom and the fluorinated groups, fluorine-containing molecules are essential. Therefore, the search for new fluorinated groups as well as straightforward and original methodologies for their installation is of prime importance. Especially, the combination of organofluorine chemistry with transition metal-catalyzed C–H bond functionalization reactions offered straightforward tools to access original fluorinated scaffolds. In this context, over the last years, our group focused on the development of original methodologies to synthesize fluorine-containing molecules with a special attention to emergent fluorinated groups. The present account highlights our recent contributions to the synthesis of highly value-added fluorine-containing compounds by transition metal-catalyzed C–H bond activation.

Transition-metal-catalyzed direct β-functionalization of simple carbonyl compounds

2014 ◽  
Vol 1 (7) ◽  
pp. 838-842 ◽  
Author(s):  
Guobing Yan ◽  
Arun Jyoti Borah
Keyword(s):  
Transition Metal ◽  
Carbonyl Compounds ◽  
Bond Activation ◽  
Active Area ◽  
Synthetic Chemistry ◽  
Chemical Transformations ◽  
Recent Advances ◽  
Direct Functionalization ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Chemical transformations via catalytic C–H bond activation have been established as one of the most powerful tools in organic synthetic chemistry. Transition-metal-catalyzed direct functionalization of β-C(sp3)–H bonds of carbonyl compounds has been developed in recent years. This highlight will focus on recent advances in this active area and their mechanisms are also discussed.

Transient- and Native-Directing-Group-Enabled Enantioselective C–H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Chuan He ◽  
Bing Zu ◽  
Yonghong Guo ◽  
Jie Ke
Keyword(s):  
Carboxylic Acid ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Short Review ◽  
Synthetic Approach ◽  
Bond Functionalization ◽  
Axial Chirality ◽  
Planar Chirality ◽  
Directing Group ◽  
Metal Catalyzed

AbstractIn recent years, transition-metal-catalyzed enantioselective C–H bond functionalization using chiral transient directing groups (cTDGs) or native directing groups (NDGs) has emerged as a powerful and attractive­ synthetic approach to streamline the synthesis of chiral molecules­. This short review focuses on recent advances on imine-based cTDGs strategies and native amine and carboxylic acid directed strategies for the asymmetric functionalization of various C–H bonds. We have endeavored to highlight the great potential of this methodology and hope that this review will inspire further research in this area.1 Introduction2 Transient-Directing-Group-Enabled Enantioselective C–H Functionalization2.1 Generation of Central Chirality2.2 Generation of Axial Chirality2.3 Generation of Planar Chirality3 Native-Directing-Group-Enabled Enantioselective C–H Functionalization3.1 Native Amines as Directing Groups3.2 Native Carboxylic Acids as Directing Groups4 Conclusions and Outlook

Enantioselective C–H Functionalization toward Silicon-Stereogenic Silanes

Synthesis ◽  
2022 ◽  
Author(s):  
Chuan He ◽  
Wei Yuan
Keyword(s):  
Transition Metal ◽  
Short Review ◽  
Synthetic Approach ◽  
Bond Functionalization ◽  
Recent Advances ◽  
Stereogenic Centers ◽  
Organosilicon Chemistry ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Shed Light

In recent years, transition-metal-catalyzed enantioselective C–H bond functionalization has emerged as a powerful and attractive synthetic approach to access silicon-stereogenic centers, which continues to give impetus for the innovation of chiral organosilicon chemistry. This short review is aimed to summarize recent advances in the construction of silicon-stereogenic silanes via transition-metal-catalyzed enantioselective C–H functionalization. We have endeavored to highlight the great potential of this methodology and hope that this review will shed light on new perspectives, inspire further research in this emerging area.

Transition-Metal-Catalyzed Oxidative and Decarboxylative Acylations through sp2 C-H Bond Activation

2015 ◽  
Vol 20 (5) ◽  
pp. 471-511 ◽  
Author(s):  
Satyasheel Sharma ◽  
Neeraj Kumar Mishra ◽  
Youngmi Shin ◽  
In Su Kim
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Hydroxylamines as One-Atom Nitrogen Sources for Metal-Catalyzed Cycloadditions

Synthesis ◽  
2021 ◽  
Author(s):  
Xinjun Luan ◽  
Jingxun Yu
Keyword(s):  
Transition Metal ◽  
Nitrogen Source ◽  
Nucleophilic Reagent ◽  
Nitrogen Sources ◽  
Short Review ◽  
Indole Derivatives ◽  
Electrophilic Amination ◽  
Intramolecular Cycloaddition ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed C–N bond formation is one of the most important pathways to synthesize N-heterocycles. Hydroxylamines can be transformed into a nucleophilic reagent to react with a carbon cation or coordinate with a transition metal; it can also become an electrophilic nitrogen source to react with arenes, alkenes, and alkynes. In this short review, the progress made on transition-metal-catalyzed cycloadditions with hydroxylamines as a nitrogen source is summarized.1 Introduction2 Cycloaddition To Form Aziridine Derivatives2.1 Intramolecular Cycloaddition To Form Aziridine Derivatives2.2 Intermolecular Cycloaddition To Form Aziridine Derivatives3 Cycloaddition To Form Indole Derivatives4 Cycloaddition To Form Other N-Heterocycles4.1 Aza-Heck-Type Amination Reactions4.2 Nitrene Insertion Amination Reactions4.3 Intramolecular Nucleophilic and Electrophilic Amination Reactions5 Conclusion and Outlook

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