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

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

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.

scholarly journals Exploration of C–H and N–H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines

2014 ◽  
Vol 10 ◽  
pp. 2186-2199 ◽  
Author(s):  
Michael Ghobrial ◽  
Marko D Mihovilovic ◽  
Michael Schnürch
Keyword(s):  
Transition Metal ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Copper Salts ◽  
Bond Functionalization ◽  
Palladium Catalyzed ◽  
Synthetic Routes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The synthesis of 1,2,3-trisubstituted indoles was investigated. More specifically, straightforward synthetic routes towards 1-(1,2-diarylindol-3-yl)-N-PG-THIQs (PG = protecting group, THIQ = tetrahydroisoquinoline) employing transition metal-catalyzed C–H and N–H-bond functionalization were explored. It was found that the synthesis of the target compounds is strongly dependent on the order of events. Hence, depending on the requirements of a synthetic problem the most suitable and promising pathway can be chosen. Additionally, a new synthetic approach towards 1,2-diarylindoles starting from 1-arylindole could be established in the course of our investigation by using a palladium-catalyzed protocol. Such 1,2-diarylindoles were successfully reacted with N-Boc-THIQ to furnish 1,2,3-trisubstituted indoles as target compounds. Furthermore, regioselective N-arylation of protected and unprotected 1-(indol-3-yl)-THIQs was successfully conducted using either simple iron or copper salts as catalysts.

Recent Advances in Transition-Metal-Catalyzed C–H Addition to Nitriles

Synthesis ◽  
2021 ◽  
Author(s):  
Wei-Wei Liao ◽  
Shu-Qiang Cui
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Recent Progress ◽  
Building Blocks ◽  
Short Review ◽  
Synthetic Approach ◽  
Bond Forming ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed C–H bond addition to nitriles has emerged as a powerful synthetic approach for the construction of C–C bonds in organic synthesis. Due to the merits of atom- and step-economy, as well the easy availability of the starting materials, these transformations not only deliver acyclic aryl ketone products with nitriles­ as C-building blocks, but can also be utilized for the highly efficient­ assembly of azaheterocyclic skeletons using nitriles as C–N building blocks. This short review summarizes recent progress on transition-metal-catalyzed C–C bond-forming reactions based on C(sp2)–H and C(sp3)–H additions to nitriles.1 Introduction2 Palladium-Catalyzed C–H Addition to Nitriles2.1 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Ketone (Imine) Products2.2 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Azaheterocycles2.3 Palladium-Catalyzed C–H Addition to Nitriles/1,2-Rearangement3 Other Transition-Metal-Catalyzed C–H Additions to Nitriles4 Summary and Outlook

Selective Synthesis of 2- and 7-Substituted Indole Derivatives via Chelation-Assisted Metallocarbenoid C–H Bond Functionalization

Synthesis ◽  
2017 ◽  
Vol 50 (02) ◽  
pp. 227-240 ◽  
Author(s):  
Sergey Osipov ◽  
Daria Vorobyeva
Keyword(s):  
Short Review ◽  
Diazo Compounds ◽  
Indole Derivatives ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Drug Candidates ◽  
Directing Group ◽  
Metal Catalyzed ◽  
Related Compounds ◽  
Made In

Functionally substituted indole derivatives are important intermediates for the synthesis of new potential drug candidates exhibiting strong bioactivities. Over the past few years, significant progress has been made in the direct C–H functionalization of the indole ring through the usage of metal-catalyzed intermolecular cross-coupling with diazo compounds. Directing group strategy provides a unique possibility for selective insertion of carbenes catalytically generated from diazo compounds into challenging indole C2–H and C7–H bonds. This short review summarizes recent advances in carbenoid functionalization of indole derivatives under chelation-controlled metal catalysis.1 Introduction2 Indole C2 Alkylation with α-Diazotized Meldrum’s Acid3 Indole C2 Alkylation with Diazomalonate Derivatives and Related Compounds4 Indole C7 Alkylation with Diazomalonates and Related Compounds5 Tandem Indole C2–H Alkylation/Cyclization6 Indoline C7 Alkylation with Diazomalonates and Related Compounds7 Tandem Indoline C7–H Alkylation/Cyclization8 Conclusion

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

scholarly journals N-Benzo[c][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide

Molbank ◽  
10.3390/m1075 ◽  
2019 ◽  
Vol 2019 (3) ◽  
pp. M1075 ◽  
Author(s):  
Hamad H. Al Mamari ◽  
Nasser Al Awaimri ◽  
Yousuf Al Lawati
Keyword(s):  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Title Compound ◽  
Structural Motif ◽  
Spectroscopic Methods ◽  
Bond Functionalization ◽  
Directing Group ◽  
Metal Catalyzed

The title compound, N-benzo[c][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide (1) was synthesized by reacting 3-trifluoromethylbenzoyl chloride (4) and 4-aminobenzo[c][1,2,5]thiadiazole (5). The compound was characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS) and its composition confirmed by elemental analysis. The importance of this compound lies in its possession of an N,N-bidentate directing group. Such a structural motif is potentially suitable for metal-catalyzed C-H bond functionalization reactions.

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