Palladium‐catalyzed cross‐coupling reactions of coumarin derivatives: An overview

Kanchana, U. S.; Diana, Elizabeth J.; Mathew, Thomas; Anilkumar, Gopinathan

doi:10.1002/aoc.5983

Cited by 35 publications

(16 citation statements)

References 75 publications

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“…[26][27][28][29] Then the [Pd 3 ] + triangles was employed in the cycloisomerization of 1, 6-enyne derivatives and enabled the efficient formation of various polycyclic frameworks through sequential cyclization/double bond shift (Scheme 1b). [30][31] Coupling reactions are one of the most powerful pathways in organic synthesis [32][33][34][35][36][37][38] and have been widely used in the synthesis of important pharmaceutical intermediates, [39][40] natural products, [41] agricultural chemicals [42] and other materials. [43][44][45] The catalytic, synthetic and pharmaceutical applications of dimer palladium have also been widely applied in this field .…”

Section: Introductionmentioning

confidence: 99%

C−I Selective Sonogashira and Heck Coupling Reactions Catalyzed by Aromatic Triangular Tri‐palladium

et al. 2022

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Aromatic triangular tri‐palladium cations 1–3, abbreviated as [Pd3]+, have shown interesting photoelectric properties, Lewis basic character, and excellent activities in catalytic hydrogenation. Herein, we report the highly efficient and C−I selective Sonogashira and Heck coupling reactions catalyzed by these tri‐palladium complexes. Benefiting from the moderate C−I bond association energy, these tri‐palladiums presented exclusive reactivities to aryl iodides over the brominated aromatics in coupling reactions. In the Sonogashira pathway, good to excellent isolated yields (71–95 %) were achieved. Gram‐scale reaction reached 93 % of yield with palladium loading as few as 0.06 mol %. We also explored the electronic and steric effects for phenyl alkynes and aryl iodides including heteroaromatics like thiophene, pyridine, pyrazole, and pyrazine. Similarly, yields of 71–96 % were obtained for palladium loading of 1.5 mol% through catalyzed Heck coupling of aryl iodides and alkenes. The HRMS monitoring revealed that [Pd3]+ maintained as whole entity during the catalytic process due to its robusness.

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Section: Introductionmentioning

confidence: 99%

C−I Selective Sonogashira and Heck Coupling Reactions Catalyzed by Aromatic Triangular Tri‐palladium

et al. 2022

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“…Initially, a majority of the reactions developed in this area were transition metal (TM)-based reactions such as Suzuki, Heck, Sonogashira, Buchwald-Hartwig, Stille, cross-dehydro-genative coupling, and decarboxylative coupling, etc. [8] Lately, CÀ H activation reactions have also made a significant mark in this category of coumarins functionalization and both metal and metal-free versions have been developed. [9] Another strategy to functionalize coumarin scaffolds involve multicomponent reactions (MCR) in which abundantly available substrates such as aldehydes, amines, amides, urea, mercaptans, cinnamyl derivatives and barbituric acids have been used.…”

Section: Introductionmentioning

confidence: 99%

Visible Light‐Induced Synthesis of Functionalized Coumarins

Singh

Sharma

2021

Adv Synth Catal

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Functionalized coumarins are privileged scaffolds which display diverse pharmacological and physiological activities, and a myriad of applications in medical science and biomedical research. Owing to these multifarious activities of coumarins, synthetic chemists are actively engaged in developing new and superior methods for their synthesis. In the last decade, the synthesis of functionalized coumarins via visible light-induced methodologies has turned into one of the most significant and fundamental missions in organic synthesis. This review covers the literature on the synthesis of functionalized coumarins under visible light-assisted methodologies. 3.6. 4-Chloro-3-Nitrocoumarin as Substrate 3.7. 1-Bromo-2H-Phenaleno[1,2,3-de]chromen-2-Ones as Substrate 4.Conclusions

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“…Catalysis is one of the fundamental pillars of green chemistry [ 22 ], and the transition-metal-catalyzed synthesis of coumarins has been reviewed by Sharma et al [ 23 ]. More recently, Kanchana et al published an account on the palladium-catalyzed cross-coupling reactions of coumarin derivatives [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric organocatalyzed synthesis of coumarin derivatives

Moreira¹,

Martelli²,

Corrêa³

2021

Beilstein J. Org. Chem.

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Coumarin derivatives are essential scaffolds in medicinal and synthetic chemistry. Compounds of this class have shown important activities, such as anticancer and antiparasitic, besides the commercially available drugs. These properties led to the development of efficient and greener synthetic methods to achieve the 2H-chromen-2-one core. In this context, the advances in asymmetric organocatalyzed synthesis of coumarin derivatives are discussed in this review, according to the mode of activation of the catalyst.

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Palladium‐catalyzed cross‐coupling reactions of coumarin derivatives: An overview

Cited by 35 publications

References 75 publications

C−I Selective Sonogashira and Heck Coupling Reactions Catalyzed by Aromatic Triangular Tri‐palladium

C−I Selective Sonogashira and Heck Coupling Reactions Catalyzed by Aromatic Triangular Tri‐palladium

Visible Light‐Induced Synthesis of Functionalized Coumarins

Asymmetric organocatalyzed synthesis of coumarin derivatives

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