Transition metal-catalyzed C–N cross-coupling reaction of bromine-substituted pyranilidene derivatives: synthesis, characterization, and optical properties study of pyran-based chromophores

2020 ◽  
Vol 17 (10) ◽  
pp. 2627-2636
Author(s):  
Keshvar Rahimpour ◽  
Hassan Zarenezhad ◽  
Reza Teimuri-Mofrad
Keyword(s):  
Optical Properties ◽  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

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 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.

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

scholarly journals Chemoselective nickel-catalyzed coupling through substrate photoexcitation

2021 ◽  
Author(s):  
Pradipta Das ◽  
Eliot Woods ◽  
Jack Ly ◽  
Jack Olding ◽  
Kayla Presley ◽  
...  
Keyword(s):  
Excited State ◽  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Ni Catalyst ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Metal Catalyzed ◽  
Coupling Mechanisms

Metallaphotoredox catalysis combines the well-established mechanisms of transition-metal-catalyzed cross-coupling reactions with one-electron redox manipulations enabled by light. In most cases, a transition metal or organic dye serves as the photoredox catalyst while a ground-state Pd or Ni catalyst performs the organometallic steps. Cross-coupling mechanisms that rely on direct photoexcitation of a light-absorbing substrate have the potential to access distinct mechanisms and deliver unique selectivity based on the substrate’s excited-state properties. In this report, we describe a photoinduced, Ni-catalyzed Suzuki–Miyaura cross coupling reaction that selectively functionalizes BODIPY chromophores, a versatile class of tunable, bright, photostable fluorophores. Using a bis-iodo BODIPY substrate, the selectivity for mono- vs. bis-arylation was found to be governed by a remote substituent that subtly alters the excited-state properties of the substrate. Consistent with a substrate photoexcitation mechanism, high chemoselectivity is also observed in mixtures of chromophores with distinct excited-state properties. This reaction is compatible with a variety of substituted BODIPY chromophores and boronic acids and esters, enabling the rapid synthesis of unsymmetrically-substituted chromophores.

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