Transition-Metal-Catalyzed Enantioselective Synthesis of Indoles from 2-Alkynylanilines

Synthesis ◽  
2022 ◽  
Author(s):  
Zhi-Shi Ye ◽  
Jin-cheng Li ◽  
Gang Wang
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Short Review ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Indole Derivatives ◽  
Cross Coupling Reaction ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Optically active indole derivatives are ubiquitous in natural products and widely recognized as privileged components in pharmacologically relevant compounds. Therefore, developing catalytic asymmetric approaches for constructing indole derivatives is highly desirable. In this short review, transition-metal-catalyzed enantioselective synthesis of indoles from 2-alkynylanilines is summarized. 1 Introduction 2 Aminometalation triggered asymmetric cross-coupling reaction/insertion 2.1 Asymmetric Cross-Coupling Reaction 2.2 Asymmetric insertion of C=O, C=C and C≡N bonds 3 Asymmetric relay catalysis 4 Conclusion

scholarly journals Recent Advances in Transition-Metal-Catalyzed, Directed Aryl C–H/N–H Cross-Coupling Reactions

Synthesis ◽  
2017 ◽  
Vol 49 (20) ◽  
pp. 4586-4598 ◽  
Author(s):  
Martyn Henry ◽  
Mohamed Mostafa ◽  
Andrew Sutherland
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Short Review ◽  
Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Amination and amidation of aryl compounds using a transition-metal-catalyzed cross-coupling reaction typically involves prefunctionalization or preoxidation of either partner. In recent years, a new class of transition-metal-catalyzed cross-dehydrogenative coupling reaction has been developed for the direct formation of aryl C–N bonds. This short review highlights the substantial progress made for ortho-C–N bond formation via transition-metal-catalyzed chelation-directed aryl C–H activation and gives an overview of the challenges that remain for directed meta- and para-selective reactions.1 Introduction2 Intramolecular C–N Cross-Dehydrogenative Coupling2.1 Nitrogen Functionality as Both Coupling Partner and Directing Group2.2 Chelating-Group-Directed Intramolecular C–N Bond Formation3 Intermolecular C–N Cross-Dehydrogenative Coupling3.1 ortho-C–N Bond Formation3.1.1 Copper-Catalyzed Reactions3.1.2 Other Transition-Metal-Catalyzed Reactions3.2 meta- and para-C–N Bond Formation4 C–N Cross-Dehydrogenative Coupling of Acidic C–H Bonds5 Conclusions

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 Metal Catalyzed Suzuki-Miyaura Cross-Coupling– Efficient Methodology for Synthesis the Natural and non-Natural biological active Molecules

2017 ◽  
Author(s):  
Hira Israr ◽  
Shazia Kaousar ◽  
Nasir Rasool ◽  
Gulraiz Ahmad ◽  
Muhammad Nazirul Mubin Aziz ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Biologically Active ◽  
Polymer Chemistry ◽  
Active Compounds ◽  
New Class ◽  
Cross Coupling Reaction ◽  
Metal Catalyzed

New class of biologically active and non-active compounds can be synthesized via transition metal mediated Suzuki cross coupling reaction that has a great impact on the advancement of organic chemistry. These resulted products can lend a helping hand in pharmaceutical and polymer chemistry for the betterment of mankind. Suzuki-Miyaura cross coupling reaction is one of the best tools through which many natural and non-natural compounds can be synthesized.

meta- and para-Functionalized Thermally Crosslinkable OLED-Materials through Selective Transition-Metal-Catalyzed Cross-Coupling Reactions

Synthesis ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 4489-4499
Author(s):  
Michael Reggelin ◽  
Matthias Hempe ◽  
Lutz Schnellbächer ◽  
Tobias Wiesner
Keyword(s):  
Transition Metal ◽  
Thermal Sensitivity ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthetic Approach ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Dsc Measurements ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials­ based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9H-fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9H-fluorenes that underwent end-functionalization by the Suzuki–Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino)-9H-fluorenes. Novel meta-functionalized materials were synthesized, which are difficult to prepare by traditional synthetic pathways. The thermal behavior of the compounds was investigated by DSC measurements, indicating a lower thermal sensitivity of the meta-substituted materials than their para-functionalized analogues.

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