Palladium catalyzed C–C and C–N bond forming reactions: an update on the synthesis of pharmaceuticals from 2015–2020

Rayadurgam, Jayachandra; Sana, Sravani; Sasikumar, M.; Gu, Qiong

doi:10.1039/d0qo01146k

Cited by 120 publications

(85 citation statements)

References 176 publications

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“…Transition metal-mediated aryl–aryl and N –aryl bond forming reactions are powerful synthetic tools for constructing highly complex molecules [ 56 , 57 ]. They have been recently employed in the key steps of the total synthesis of nitrogen containing natural products, as well as for the construction of heterocycles in medicinal chemistry in a one-pot fashion or multi step processes due to high efficiency and compatibility with numerous functional groups.…”

Section: Simultaneous Aryl–aryl and N –Aryl Coupling Reactions For Phenanthridinone Synthesismentioning

confidence: 99%

Synthetic Strategies in the Preparation of Phenanthridinones

et al. 2021

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Phenanthridinones are important heterocyclic frameworks present in a variety of complex natural products, pharmaceuticals and displaying wide range of pharmacological actions. Its structural importance has evoked a great deal of interest in the domains of organic synthesis and medicinal chemistry to develop new synthetic methodologies, as well as novel compounds of pharmaceutical interest. This review focuses on the synthesis of phenanthridinone scaffolds by employing aryl-aryl, N-aryl, and biaryl coupling reactions, decarboxylative amidations, and photocatalyzed reactions.

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Section: Simultaneous Aryl–aryl and N –Aryl Coupling Reactions For Phenanthridinone Synthesismentioning

confidence: 99%

Synthetic Strategies in the Preparation of Phenanthridinones

et al. 2021

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“…showed the significance of using copper as a catalyst for N‐arylation of sulfoximines with aryl halides, where copper iodide (II) as a catalyst and cesium carbonate or cesium acetate as a base in DMSO at 90 °C, cross‐coupling of N−H sulfoximines with aryl iodides and bromides furnished the corresponding N‐arylated sulfoximines. Although N‐arylation of haloarenes with electron withdrawing groups (EWG) by Pd (0) catalyst has been very well addressed in literature, there are some limitations with fluoroarenes (EWG) [32–36] . So as to address this, our group designed a copper‐exchanged fluorapatite (CuFAP) and copper‐exchanged tert‐butoxyapatite (CuTBAP) catalysts by incorporation of basic species in hydroxyapatite using NH 4 F and potassium tert‐butoxide and then by subsequent exchange with copper (II) salt [19] .…”

Section: Copper‐apatite Catalystmentioning

confidence: 99%

Transition Metal Exchanged Hydroxyapatite/Fluorapatite Catalysts for C−C and C−N Bond Forming Reactions

Gadipelly

Deshmukh

Mannepalli

2021

The Chemical Record

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Transition metal (Cu, Zn, Rh, Pd) exchanged hydroxyapatite (HAP)/fluorapatite (FAP) materials have been synthesized by ion‐exchange method resulting in incorporation of the metal ions in the HAP/FAP structure. C−C and C−N bond forming reactions are important in synthetic organic chemistry as these organic transformations are very critical. Transition metal exchanged FAP provides an efficient catalytic system for N‐arylation of haloarenes and Suzuki and Heck coupling of haloarenes. By designing such catalytic materials, our group has developed synthetic methods which allow higher product yields and easy separation with the use of a small amount of catalyst in a shorter reaction time. This account addresses the work carried out in last two decades in the area of C−C and C−N bond forming reactions using transition metal exchanged fluorapatite.

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“…Among these cross‐coupling reactions, one of the most widely explored reactions is the C−C cross coupling reactions which finds variety of application in the field of industry, medicine, and agriculture. Various C−C coupling reactions like Sonogashira coupling, [7] Negishi coupling, [8] Stille coupling, [9] Suzuki‐Miyaura coupling, [10] Mizoroki‐Heck (MH) coupling [11] and Buchwald‐Hartwig coupling reactions [12] are nowadays extensively used for several synthetic strategies ranging from polymer development to pharmaceuticals and natural products [13] …”

Section: Introductionmentioning

confidence: 99%

Recent Advances on N‐Heterocyclic Carbene‐Palladium‐catalyzed Heck Reaction

2022

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Heck reaction is a synthetically important C−C bond forming coupling reaction happening between alkenes and aryl or vinyl halides catalyzed by palladium complexes to form substituted alkenes. This review focusses on the recent advancements in the development of various types of N‐heterocyclic carbene (NHC) ligands coupled with palladium catalyst that can catalyze Mizoroki‐Heck reactions. NHC ligands have unique characteristic nature, and hence widely used in homogeneous catalysis. Generally, they have good σ‐donating and sparingly π‐accepting properties. It is more stable and shows superior π‐accepting properties when compared to phosphine ligands that is under prominent studies. Thus, they can stabilize large extend of metal oxidation states and have high thermal stability. Most of the catalysts outlined here provide efficient and green synthetic route for the development of C−C coupled bond formations. The review encompasses literature from 2017 to 2021.

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Palladium catalyzed C–C and C–N bond forming reactions: an update on the synthesis of pharmaceuticals from 2015–2020

Abstract: Some of the most prominent and promising catalysts in organic synthesis for the requisite construction of C–C and C–N bonds are palladium (Pd) catalysts, which play a pivotal role in pharmaceutical and medicinal chemistry.

Cited by 120 publications

References 176 publications

Synthetic Strategies in the Preparation of Phenanthridinones

Synthetic Strategies in the Preparation of Phenanthridinones

Transition Metal Exchanged Hydroxyapatite/Fluorapatite Catalysts for C−C and C−N Bond Forming Reactions

Recent Advances on N‐Heterocyclic Carbene‐Palladium‐catalyzed Heck Reaction

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