The Homocoupling Reaction of Aromatic Terminal Alkynes by a Highly Active Palladium(II)/AgNO3 Cocatalyst in Aqueous Media Under Aerobic Conditions

Guo, Mengping; Chen, Bin; Lv, Meiyun; Zhou, Xiuling; Wen, Yuh‐Sheng; Shen, Xiuli

doi:10.3390/molecules21050606

Cited by 10 publications

(6 citation statements)

References 35 publications

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“…Further elongation of the chain (i.e., synthesis of poly-ynes can be achieved by Hagihara-Sonogashira coupling of diethynylarylenes and dihaloarylenes or transition metal-catalyzed metathesis of diy-nes) . For the polymerization of substituted acetylenes, transition metals, − post-transition metals and MOF-catalyzed methods have also been reported. Thermal or light assisted metal–surface-mediated C–H activation has also attracted the attention of chemists to realize carbon-based scaffolds and two-dimensional materials with a high degree of structural control. , For this purpose, metals with low-Miller index surfaces are utilized. − Among nonchemical methods, the generation of oligo-ynes has also been reported using fs and ns lasers. , Kitaura et al .…”

Section: Synthesismentioning

confidence: 99%

Rise of Conjugated Poly-ynes and Poly(Metalla-ynes): From Design Through Synthesis to Structure–Property Relationships and Applications

et al. 2018

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Conjugated poly-ynes and poly(metalla-ynes) constitute an important class of new materials with potential application in various domains of science. The key factors responsible for the diverse usage of these materials is their intriguing and tunable chemical and photophysical properties. This review highlights fascinating advances made in the field of conjugated organic poly-ynes and poly(metalla-ynes) incorporating group 4-11 metals. This includes several important aspects of conjugated poly-ynes viz. synthetic protocols, bonding, electronic structure, nature of luminescence, structure-property relationships, diverse applications, and concluding remarks. Furthermore, we delineated the future directions and challenges in this particular area of research.

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Section: Synthesismentioning

confidence: 99%

Rise of Conjugated Poly-ynes and Poly(Metalla-ynes): From Design Through Synthesis to Structure–Property Relationships and Applications

et al. 2018

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“…Thereafter, some interesting [Cu]-catalyzed approaches have been developed. Though Glaser coupling was well established under [Cu]-catalysis, there are a few reports by using other transition-metal-catalysts, such as Pd-Cu, 32,33 Pd-Ag, 34 Pd, 25,35 Ni, 36 Au, 37,38 etc. Herein, we intended to check the applicability of present PdO/GO catalyst for Glaser coupling.…”

Section: Resultsmentioning

confidence: 99%

Organic transformations catalyzed by palladium nanoparticles on carbon nanomaterials

et al. 2018

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An efficient CC bond coupling reactions (Suzuki-Miyaura and Glaser) catalyzed by PdO/GO nano-catalyst is presented. In addition, PdO/MWCNT nano-catalyst-mediated domino one-pot synthesis of 2-alkyl/2-aryl benzofurans has been accomplished from 2-iodophenols and terminal alkynes. The formation of benzofurans proceeds through intermolecular Sonogashira reaction followed by intramolecular nucleophilic addition of internal hydroxyl group onto the acetylenic bond. The catalyst PdO/GO has been reused successfully, with nearly no loss of activity up to 5 cycles.

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“…Alternatively, a P,O-chelate Pd(II) 48/AgNO 3 co-catalytic system was employed for the oxidative dimerization of aromatic terminal alkynes with Et 3 N as the base in an aqueous medium under an ambient atmosphere (Scheme 41b). 68 Prior to this, Guo's group 69 had achieved a Pd(II)/AgNO 3 -co-catalyzed oxidative dimerization of aromatic terminal alkynes to afford satisfactory yields of the corresponding 1,3-diynes by using the palladium(II) complex 49, which was synthesized in an aqueous medium under aerobic conditions (Scheme 42).…”

Section: Short Review Synthesismentioning

confidence: 99%

Palladium-Catalyzed Homo-Dimerization of Terminal Alkynes

et al. 2023

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The palladium-catalyzed homo-dimerization of terminal alkynes is a powerful and atom economic method for the preparation of highly unsaturated four carbon skeletons, which are key structural units found in natural and/or biologically active products and materials. In homo-dimerization of terminal alkynes, a major issue is the control of chemo-, regio-, and stereoselectivity. For this effort, over the past few decades, various strategies and methods have been developed in palladium catalytic systems. Herein, we highlight prominent methods for the selective synthesis of these valuable compounds including conjugate 1,3-enynes, 1,3-diynes, and 1,3-dienes. 1 Introduction 2 Redox-Neutral Homo-Dimerization of Terminal Alkynes to 1,3-Enynes 2.1 Head to Head Dimerization 2.2 Head to Tail Dimerization 3 Oxidative Homo-Dimerization of Terminal Alkynes to 1,3-Diynes 3.1 Unsupported Palladium Catalysts 3.1.1 Choice of Oxidant 3.1.2 Choice of Ligand 3.1.3 Choice of Solvent 3.2 Supported Palladium Catalysts 4 Reductive Homo-Dimerization of Terminal Alkynes to 1,3-Dienes 5 Conclusion

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The Homocoupling Reaction of Aromatic Terminal Alkynes by a Highly Active Palladium(II)/AgNO3 Cocatalyst in Aqueous Media Under Aerobic Conditions

Cited by 10 publications

References 35 publications

Rise of Conjugated Poly-ynes and Poly(Metalla-ynes): From Design Through Synthesis to Structure–Property Relationships and Applications

Rise of Conjugated Poly-ynes and Poly(Metalla-ynes): From Design Through Synthesis to Structure–Property Relationships and Applications

Organic transformations catalyzed by palladium nanoparticles on carbon nanomaterials

Palladium-Catalyzed Homo-Dimerization of Terminal Alkynes

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