Skip to content
2000
image of Utility of Palladium as a Catalyst for the Synthesis of Five and Six-Membered Heterocyclic Moieties

Abstract

Heterocyclic chemistry is crucial, representing approximately fifty percent of all established organic compounds. Five and six-membered heterocyclic moieties such as pyrrole, thiazole, imidazole, oxadiazole, pyridine, piperazine, and pyrimidine have been reported with a wide range of pharmacological activities. In modern chemistry, palladium-catalyzed reactions have emerged as a powerful tool for synthesizing different heterocyclic moieties, as they provide high stereoselectivity and regioselectivity. Palladium is an effective, environmentally friendly, and cost-effective metal with diverse scopes in organic synthesis. It offers efficient and precise methods for developing diverse molecular structures and potential drug molecules. Palladium-catalyzed reactions comprised C-C cross-coupling, C-N cross-coupling, C-H activation, cyclization, etc. The present manuscript provides insights into recently reported methods for the synthesis of 5 and 6-membered heterocyclic moieties where palladium was utilized as a catalyst.

Loading

Article metrics loading...

/content/journals/coc/10.2174/0113852728404183251203015241
2026-02-20
2026-02-27
Loading full text...

Full text loading...

References

  1. Rani S. Raheja K. Luxami V. Paul K. A review on diverse heterocyclic compounds as the privileged scaffolds in non-steroidal aromatase inhibitors. Bioorg. Chem. 2021 113 105017 10.1016/j.bioorg.2021.105017 34091288
    [Google Scholar]
  2. Goswami N. Bhattacharya T. Maiti D. Transient directing ligands for selective metal-catalysed C-H activation. Nat. Rev. Chem. 2021 5 9 646 659 10.1038/s41570‑021‑00311‑3 37118417
    [Google Scholar]
  3. Zhao X. Chang Y. Chen W.J. Wu Q. Pan X. Chen K. Weng B. Recent progress in Pd-based nanocatalysts for selective hydrogenation. ACS Omega 2022 7 1 17 31 10.1021/acsomega.1c06244 35036674
    [Google Scholar]
  4. Shabir G. Shafique I. Saeed A. Ultrasound assisted synthesis of 5-7 membered heterocyclic rings in organic molecules. J. Heterocycl. Chem. 2022 59 10 1669 1702 10.1002/jhet.4527
    [Google Scholar]
  5. Rayadurgam J. Sana S. Sasikumar M. Gu Q. Palladium catalyzed C-C and C-N bond forming reactions: An update on the synthesis of pharmaceuticals from 2015-2020. Org. Chem. Front. 2021 8 2 384 414 10.1039/D0QO01146K
    [Google Scholar]
  6. Bhattacharya T. Ghosh A. Maiti D. Hexafluoroisopropanol: The magical solvent for Pd-catalyzed C-H activation. Chem. Sci. 2021 12 11 3857 3870 10.1039/D0SC06937J 34163654
    [Google Scholar]
  7. Mermer A. Keles T. Sirin Y. Recent studies of nitrogen containing heterocyclic compounds as novel antiviral agents: A review. Bioorg. Chem. 2021 114 105076 10.1016/j.bioorg.2021.105076 34157555
    [Google Scholar]
  8. Holman K.R. Stanko A.M. Reisman S.E. Palladium-catalyzed cascade cyclizations involving C-C and C-X bond formation: Strategic applications in natural product synthesis. Chem. Soc. Rev. 2021 50 14 7891 7908 10.1039/D0CS01385D 34037626
    [Google Scholar]
  9. Chernyshev V.M. Ananikov V.P. Nickel and palladium catalysis: Stronger demand than ever. ACS Catal. 2022 12 2 1180 1200 10.1021/acscatal.1c04705
    [Google Scholar]
  10. Mallappa.; Chahar, M.; Choudhary, N. Recent advances in the synthesis of nitrogen-containing heterocyclic compounds via multicomponent reaction and their emerging biological applications: A review. J. Iran Chem. Soc. 2025 22 1 33 10.1007/s13738‑024‑03142‑3
    [Google Scholar]
  11. Kumar N. Goel N. Heterocyclic compounds: Importance in anticancer drug discovery. Anticancer. Agents Med. Chem. 2022 22 19 3196 3207 10.2174/1871520622666220404082648 35379130
    [Google Scholar]
  12. Kabir E. Uzzaman M. A review on biological and medicinal impact of heterocyclic compounds. Results Chem. 2022 4 100606 10.1016/j.rechem.2022.100606
    [Google Scholar]
  13. Kale V.T. Burghate A.S. Wadhal S.A. Synthesis and antibacterial activity of n-heterocyclic substituted hydrazone Schiff’s bases. Indo. Am. J. Pharm. Sci. 2016 6 6404 10.13140/RG.2.2.27818.13763
    [Google Scholar]
  14. Yadav R.K. Kumar R. Singh H. Mazumdar A. Salahuddin; Chauhan, B.; Abdullah, M.M. Recent insights on synthetic methods and pharmacological potential in relation with structure of benzothiazoles. Med. Chem. 2023 19 4 325 360 10.2174/1573406418666220820110551 35993459
    [Google Scholar]
  15. Kumar R. Singh H. Yadav R.K. Mazumder A. Salahuddin; Chauhan, B.; Abdullah, M.M. Insight into the synthesis, biological activity, and structure-activity relationship of benzothiazole and benzothiazole-hydrazone derivatives: A comprehensive review. Mini Rev. Med. Chem. 2023 23 5 537 575 10.2174/1389557522666220523110521 35616666
    [Google Scholar]
  16. Ogawa Y. Tokunaga E. Kobayashi O. Hirai K. Shibata N. Current contributions of organofluorine compounds to the agrochemical industry. iScience 2020 23 9 101467 10.1016/j.isci.2020.101467 32891056
    [Google Scholar]
  17. Karki S. Structural and electronic properties of palladium and palladium doped graphene. Int. J. Sci. Res. Phys. Appl. Sci. 2023 11 37 42
    [Google Scholar]
  18. Sharma S. Krishna Kumar A.S. Rajesh N. A perspective on diverse adsorbent materials to recover precious palladium and the way forward. RSC Advances 2017 7 82 52133 52142 10.1039/C7RA10153H
    [Google Scholar]
  19. Albano G. Palladium-catalyzed cross-dehydrogenative coupling of (hetero)arenes. Org. Chem. Front. 2024 11 5 1495 1622 10.1039/D3QO01925J
    [Google Scholar]
  20. Michałek T. Hessel V. Wojnicki M. Production, recycling and economy of palladium: A critical review. Materials 2023 17 1 45 10.3390/ma17010045 38203899
    [Google Scholar]
  21. Gurunathan S. Qasim M. Park C.H. Arsalan Iqbal M. Yoo H. Hwang J.H. Uhm S.J. Song H. Park C. Choi Y. Kim J.H. Hong K. Cytotoxicity and transcriptomic analyses of biogenic palladium nanoparticles in human ovarian cancer cells (SKOV3). Nanomaterials 2019 9 5 787 10.3390/nano9050787 31121951
    [Google Scholar]
  22. Chong Y. Dai X. Fang G. Wu R. Zhao L. Ma X. Tian X. Lee S. Zhang C. Chen C. Chai Z. Ge C. Zhou R. Palladium concave nanocrystals with high-index facets accelerate ascorbate oxidation in cancer treatment. Nat. Commun. 2018 9 1 4861 10.1038/s41467‑018‑07257‑z 30451824
    [Google Scholar]
  23. Ndaya C. Javahiraly N. Brioude A. Recent advances in palladium nanoparticles-based hydrogen sensors for leak detection. Sensors 2019 19 20 4478 10.3390/s19204478 31623081
    [Google Scholar]
  24. Tang L. Huan K. Deng D. Han L. Zeng Z. Luo L. Glucose sensor based on Pd nanosheets deposited on Cu/Cu2O nanocomposites by galvanic replacement. Colloids Surf. B Biointerfaces 2020 188 110797 10.1016/j.colsurfb.2020.110797 31958621
    [Google Scholar]
  25. Hazarika M. Borah D. Bora P. Silva A.R. Das P. Biogenic synthesis of palladium nanoparticles and their applications as catalyst and antimicrobial agent. PLoS One 2017 12 9 0184936 10.1371/journal.pone.0184936 28957342
    [Google Scholar]
  26. McCarthy S. Braddock D.C. Wilton-Ely J.D.E.T. Strategies for sustainable palladium catalysis. Coord. Chem. Rev. 2021 442 213925 10.1016/j.ccr.2021.213925
    [Google Scholar]
  27. Biffis A. Centomo P. Del Zotto A. Zecca M. Pd metal catalysts for cross-couplings and related reactions in the 21st century: A critical review. Chem. Rev. 2018 118 4 2249 2295 10.1021/acs.chemrev.7b00443 29460627
    [Google Scholar]
  28. Kumbhar A. Functionalized nitrogen ligands (C N) for palladium catalyzed cross-coupling reactions (part II). J. Organomet. Chem. 2019 881 79 129 10.1016/j.jorganchem.2018.09.020
    [Google Scholar]
  29. Pagliaro M. Pandarus V. Ciriminna R. Béland F. Demma Carà P. Heterogeneous versus homogeneous palladium catalysts for cross‐coupling reactions. ChemCatChem 2012 4 4 432 445 10.1002/cctc.201100422
    [Google Scholar]
  30. Chen Q.A. Ye Z.S. Duan Y. Zhou Y.G. Homogeneous palladium-catalyzed asymmetric hydrogenation. Chem. Soc. Rev. 2013 42 2 497 511 10.1039/C2CS35333D 23138972
    [Google Scholar]
  31. Zeni G. Larock R.C. Synthesis of heterocycles via palladium-catalyzed oxidative addition. Chem. Rev. 2006 106 11 4644 4680 10.1021/cr0683966 17091931
    [Google Scholar]
  32. Ikram H. Rasool N. Zubair M. Khan K. Abbas Chotana G. Akhtar M. Abu N. Alitheen N. Elgorban A. Rana U. Efficient double suzuki cross-coupling reactions of 2, 5-dibromo-3-hexylthiophene: Anti-tumor, haemolytic, anti-thrombolytic and biofilm inhibition studies. Molecules 2016 21 8 977 10.3390/molecules21080977 27472312
    [Google Scholar]
  33. King A.K. Brar A. Li G. Findlater M. Homogeneous and recyclable palladium catalysts: Application in Suzuki-Miyaura cross-coupling reactions. Organometallics 2023 42 17 2353 2358 10.1021/acs.organomet.3c00231
    [Google Scholar]
  34. Liu L. Doucet H. Palladium‐catalyzed heck type regioselective β ‐Vinylation of thiophenes using a bromo substituent as traceless directing group. Eur. J. Org. Chem. 2024 27 4 202300986 10.1002/ejoc.202300986
    [Google Scholar]
  35. Haiouani K. Hegazy S. Alsaeedi H. Bechelany M. Barhoum A. Optimization of palladium-catalyzed one-pot synthesis of functionalized furans for high-yield production: A study of catalytic and reaction parameters. Catalysts 2024 14 10 712 10.3390/catal14100712
    [Google Scholar]
  36. Gao Y. Feng C. Seo T. Kubota K. Ito H. Efficient access to materials-oriented aromatic alkynes via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems. Chem. Sci. 2022 13 2 430 438 10.1039/D1SC05257H 35126975
    [Google Scholar]
  37. Yang J. Wang C. Xie X. Li H. Li E. Li Y. Pd/Cu-catalyzed cascade Sonogashira coupling/cyclization reactions to highly substituted 3-formyl furans. Org. Biomol. Chem. 2011 9 5 1342 1346 10.1039/c0ob00985g 21225082
    [Google Scholar]
  38. Horbaczewskyj C.S. Fairlamb I.J.S. Pd-catalyzed cross-couplings: On the importance of the catalyst quantity descriptors, mol% and ppm. Org. Process Res. Dev. 2022 26 8 2240 2269 10.1021/acs.oprd.2c00051 36032362
    [Google Scholar]
  39. Düker J. Philipp M. Lentner T. Cadge J.A. Lavarda J.E.A. Gschwind R.M. Sigman M.S. Ghosh I. König B. Cross-coupling reactions with nickel, visible light, and tert-butylamine as a bifunctional additive. ACS Catal. 2024 14 12345 12356 10.1021/acscatal.4c07185
    [Google Scholar]
  40. Bosiak M.J. Zielińska A.A. Trzaska P. Kędziera D. Adams J. Buchwald-hartwig amination of aryl halides with heterocyclic amines in the synthesis of highly fluorescent benzodifuran-based star-shaped organic semiconductors. J. Org. Chem. 2021 86 24 17594 17605 10.1021/acs.joc.1c01583 34860523
    [Google Scholar]
  41. Pu X. Zhang Y. Su M. He X. Qiu L. Palladium-catalyzed selective Buchwald-Hartwig C-N coupling of chloroaryl triflates with amines. Tetrahedron Lett. 2024 142 155096 10.1016/j.tetlet.2024.155096
    [Google Scholar]
  42. Bai J. Xu N. Wang H. Luan X. Palladium(II)-catalyzed [2+2+1] annulation of alkynes and hydroxylamines: A rodox-neutral approach to fully substituted pyrroles. Org. Lett. 2022 24 28 5099 5104 10.1021/acs.orglett.2c01925 35819925
    [Google Scholar]
  43. Zhang X. Chang M. Xu X. Zhao Q. Direct access to furan and cyclopropane derivatives via palladium-catalyzed C-H activation/alkene insertion/annulation. Chem. Commun. 2024 60 53 6769 6772 10.1039/D4CC01964D 38864642
    [Google Scholar]
  44. Ambethkar S. Padmini V. Bhuvanesh N. A one-pot sequential five-component domino reaction for the expedient synthesis of polysubstituted pyrroles. New J. Chem. 2016 40 5 4705 4709 10.1039/C5NJ03444B
    [Google Scholar]
  45. Hamasaka G. Roy D. Tazawa A. Uozumi Y. Arylation of terminal alkynes by aryl iodides catalyzed by a parts-per-million loading of palladium acetate. ACS Catal. 2019 9 12 11640 11646 10.1021/acscatal.9b04593
    [Google Scholar]
  46. Thomas A.M. Sujatha A. Anilkumar G. Recent advances and perspectives in copper-catalyzed Sonogashira coupling reactions. RSC Advances 2014 4 42 21688 21698 10.1039/C4RA02529F
    [Google Scholar]
  47. Yamada T. Hashimoto Y. Tanaka K. Morita N. Tamura O. Cationic palladium(ii)-catalyzed synthesis of substituted pyridines from α,β-unsaturated oxime ethers. RSC Advances 2022 12 33 21548 21557 10.1039/D2RA03875G 36043185
    [Google Scholar]
  48. Sweeney J.B. Doulcet J. Thapa B. Synthesis of 3-substituted pyrrolidines via palladium-catalyzed hydroarylation. iScience 2018 9 328 336 10.1016/j.isci.2018.10.025 30448732
    [Google Scholar]
  49. Li M. Li J. Zhang Z. Chen L. Ma N. Liu Q. Zhang X. Zhang G. Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles. RSC Advances 2023 13 39 27158 27166 10.1039/D3RA05440C 37701284
    [Google Scholar]
  50. Chopra J. Goswami A.K. Baroliya P.K. An overview of solid supported palladium and nickel catalysts for CC cross coupling reactions. Mini Rev. Org. Chem. 2020 17 5 589 604 10.2174/1570193X16666190617160339
    [Google Scholar]
  51. Badade S.M. Varale A.S. Thopate S.R. Manjare S.B. Plant-aided biosynthesized heterogeneous palladium nanoparticles-catalyzed suzuki coupling reaction: A review. Curr. Green Chem. 2025 12 1 60 74 10.2174/0122133461320577240724100847
    [Google Scholar]
  52. Sunbal A. Alamzeb M. Omer M. Abid O-U-R. Ullah M. Sohail M. Ullah I. Chemical insights into the synthetic chemistry of five-membered saturated heterocycles-a transition metal-catalyzed approach. Front Chem. 2023 11 1185669 10.3389/fchem.2023.1185669 37564110
    [Google Scholar]
  53. Ram V.J. Sethi A. Nath M. Pratap R. The chemistry of heterocycles: Chemistry of six to eight membered N, O, S, P and Se heterocycles. Amsterdam, Netherlands Elsevier 2019
    [Google Scholar]
  54. Chaucer P. Sharma P.K. Study of thiazines as potential anticancer agents. Plant Arch. 2020 20 3199 3202
    [Google Scholar]
  55. Ruiz-Castillo P. Buchwald S.L. Applications of palladium-catalyzed C-N cross-coupling reactions. Chem. Rev. 2016 116 19 12564 12649 10.1021/acs.chemrev.6b00512 27689804
    [Google Scholar]
  56. Nikoshvili L.Z. Matveeva V.G. Recent progress in Pd-catalyzed tandem processes. Catalysts 2023 13 8 1213 10.3390/catal13081213
    [Google Scholar]
  57. Heravi M.M. Zadsirjan V. Malmir M. Mohammadi L. Buchwald-Hartwig reaction: An update. Monatsh. Chem. 2021 152 10 1127 1171 10.1007/s00706‑021‑02834‑3
    [Google Scholar]
  58. Lu C.J. Xu Q. Feng J. Liu R.R. The asymmetric Buchwald-Hartwig amination reaction. Angew. Chem. Int. Ed. 2023 62 9 202216863 10.1002/anie.202216863 36535894
    [Google Scholar]
  59. Yu X. Zhang Z.Z. Niu J.L. Shi B.F. Coordination-assisted, transition-metal-catalyzed enantioselective desymmetric C-H functionalization. Org. Chem. Front. 2022 9 5 1458 1484 10.1039/D1QO01884A
    [Google Scholar]
  60. Corio A. Gravier-Pelletier C. Busca P. Regioselective functionalization of quinolines through C-H activation: A comprehensive review. Molecules 2021 26 18 5467 10.3390/molecules26185467 34576936
    [Google Scholar]
  61. Scott N.W.J. Ford M.J. Schotes C. Parker R.R. Whitwood A.C. Fairlamb I.J.S. The ubiquitous cross-coupling catalyst system ‘Pd(OAc)2’/2PPh3 forms a unique dinuclear PdI complex: An important entry point into catalytically competent cyclic Pd3 clusters. Chem. Sci. 2019 10 34 7898 7906 10.1039/C9SC01847F
    [Google Scholar]
  62. Schäfer G. Fleischer T. Ahmetovic M. Abele S. Development of a scalable route for a key thiadiazole building block via sequential sandmeyer bromination and room-temperature suzuki-miyaura coupling. Org. Process Res. Dev. 2020 24 2 228 234 10.1021/acs.oprd.9b00495
    [Google Scholar]
  63. Joy J. Demina T.D. Durgi A.K. Vijayan A. A brief review on the palladium-catalyzed C-H activation reactions of 2-phenylpyridines. RSC Advances 2025 15 14 11065 11084 10.1039/D5RA01203A 40201210
    [Google Scholar]
  64. Ma K. Martin B.S. Yin X. Dai M. Natural product syntheses via carbonylative cyclizations. Nat. Prod. Rep. 2019 36 1 174 219 10.1039/C8NP00033F 29923586
    [Google Scholar]
  65. Perrone S. Troisi L. Salomone A. Heterocycle synthesis through Pd‐catalyzed carbonylative coupling. Eur. J. Org. Chem. 2019 2019 29 4626 4643 10.1002/ejoc.201900439
    [Google Scholar]
  66. Ghosh T. Biswas D. Bhakta S. Palladium‐catalyzed synthesis of fused carbo‐and heterocycles. Chem. Asian J. 2022 17 21 202200725 10.1002/asia.202200725 36065137
    [Google Scholar]
  67. Isahak W.N.R.W. Al-Amiery A. Catalysts driving efficiency and innovation in thermal reactions: A comprehensive review. Green Technol. Sustain. 2024 2 6 100078 10.1016/j.grets.2024.100078
    [Google Scholar]
  68. Taleb B. Jahjah R. Cornu D. Bechelany M. Al Ajami M. Kataya G. Hijazi A. El-Dakdouki M.H. Exploring hydrogen sources in catalytic transfer hydrogenation: A review of unsaturated compound reduction. Molecules 2023 28 22 7541 10.3390/molecules28227541 38005261
    [Google Scholar]
  69. Zhang S. He X. Ding Y. Shi Z. Wu B. Supply and demand of platinum group metals and strategies for sustainable management. Renew. Sustain. Energy Rev. 2024 204 114821 10.1016/j.rser.2024.114821
    [Google Scholar]
  70. Whyte A. Bajohr J. Arora R. Torelli A. Lautens M. Sequential Pd 0 ‐ and Pd II ‐Catalyzed cyclizations: Enantioselective heck and nucleopalladation reactions. Angew. Chem. 2021 133 37 20393 20398 10.1002/ange.202106518
    [Google Scholar]
  71. Kumar A. Kumar M. Verma A.K. Well-defined palladium N-heterocyclic carbene complexes: Direct C-H Bond arylation of heteroarenes. J. Org. Chem. 2020 85 21 13983 13996 10.1021/acs.joc.0c02024 33064481
    [Google Scholar]
  72. Zhang X. Wang Y. Wang Y. Wang F. Metal nanoparticle‐catalyzed alkyne cyclization for the synthesis of heterocycles. Adv. Synth. Catal. 2024 366 202400423 10.1002/adsc.20240042
    [Google Scholar]
  73. Aydin F. Ozturk B. Yilmaz S. Sahin E. Gürbüz S. Gül B. A new air-stable Pd-PEPPSI N-heterocyclic carbene complex: Synthesis, characterization, and catalytic activity in Suzuki-Miyaura cross-coupling reactions. J. Mol. Struct. 2024 1295 135595 10.1016/j.molstruc.2024.135595
    [Google Scholar]
  74. Xu X. Feng H. Van der Eycken E.V. Microwave-assisted palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade of oxazolidines to isoquinolines. Org. Lett. 2021 23 16 6578 6582 10.1021/acs.orglett.1c02416 34379418
    [Google Scholar]
  75. Yuan S. Zhang D.Q. Zhang J.Y. Yu B. Liu H-M. Wang F. Palladium-catalyzed ligand-free double cyclization reactions for the synthesis of 3-(1′-Indolyl)-phthalides. Org. Lett. 2020 22 3 814 817 10.1021/acs.orglett.9b04241
    [Google Scholar]
  76. Inamoto K. Synthesis of heterocyclic compounds through palladium-catalyzed C-H cyclization processes. Chem. Pharm. Bull. 2013 61 10 987 996 10.1248/cpb.c13‑00420 24088691
    [Google Scholar]
  77. Shirai T. Migitera Y. Nakajima R. Kumamoto T. Palladium-catalyzed reductive heck hydroarylation of unactivated alkenes using hydrosilane at room temperature. J. Org. Chem. 2024 89 4 2787 2793 10.1021/acs.joc.3c02488 38301250
    [Google Scholar]
  78. Park Y. Kim Y. Chang S. Transition metal-catalyzed C-H amination: Scope, mechanism, and applications. Chem. Rev. 2017 117 13 9247 9301 10.1021/acs.chemrev.6b00644 28051855
    [Google Scholar]
  79. Li W.C. Zhang L. Bai S. Zhao J.H. Liu G.R. Lan Y. Chen S. Ming J. Synthesis of benzoheterocycles by palladium-catalyzed migratory cyclization through an unexpected reaction cascade. Nat. Commun. 2025 16 1 3367 10.1038/s41467‑025‑58633‑5 40204738
    [Google Scholar]
  80. Peng J. Gao Y. Zhu C. Liu B. Gao Y. Hu M. Wu W. Jiang H. Synthesis of polysubstituted 3-amino pyrroles via palladium-catalyzed multicomponent reaction. J. Org. Chem. 2017 82 7 3581 3588 10.1021/acs.joc.7b00098 28303718
    [Google Scholar]
  81. Zhang X. Xu X. Chen G. Yi W. Regioselective synthesis of 2, 3, 4-trisubstituted pyrroles via Pd (II)-catalyzed three-component cascade reactions of amines, alkyne esters, and alkenes. Org. Lett. 2016 18 19 4864 4867 10.1021/acs.orglett.6b02325 27623160
    [Google Scholar]
  82. Pan D. Wei Y. Shi M. Pd (II)-catalyzed tandem heterocyclization of 1-(1-alkynyl) cyclopropyl oxime derivatives for the synthesis of functionalized pyrroles. Org. Lett. 2016 18 15 3930 3933 10.1021/acs.orglett.6b02068 27456783
    [Google Scholar]
  83. Schitter T. Stammwitz S. Jones P.G. Werz D.B. An anti-carbopalladation/amination cascade with alkynes: Access to tetrasubstituted enamines and pyrroles. Org. Lett. 2019 21 23 9415 9419 10.1021/acs.orglett.9b03625 31742412
    [Google Scholar]
  84. Fu L. Liu Y. Wan J.P. Pd-catalyzed triple-fold C (sp2)-H activation with enaminones and alkenes for pyrrole synthesis via hydrogen evolution. Org. Lett. 2021 23 11 4363 4367 10.1021/acs.orglett.1c01301 34013729
    [Google Scholar]
  85. Tong W. Li W.H. He Y. Mo Z.Y. Tang H.T. Wang H.S. Pan Y.M. Palladium-metalated porous organic polymers as recyclable catalysts for the chemioselective synthesis of thiazoles from thiobenzamides and isonitriles. Org. Lett. 2018 20 8 2494 2498 10.1021/acs.orglett.8b00886 29620903
    [Google Scholar]
  86. Chen B. Guo S. Guo X. Zhang G. Yu Y. Selective access to 4-substituted 2-aminothiazoles and 4-substituted 5-thiocyano-2-aminothiazoles from vinyl azides and potassium thiocyanate switched by palladium and iron catalysts. Org. Lett. 2015 17 19 4698 4701 10.1021/acs.orglett.5b02152 26372853
    [Google Scholar]
  87. Dai L. Yu S. Lv N. Ye X. Shao Y. Chen Z. Chen J. Synthesis of imidazoles and oxazoles via a palladium-catalyzed decarboxylative addition/cyclization reaction sequence of aromatic carboxylic acids with functionalized aliphatic nitriles. Org. Lett. 2021 23 15 5664 5668 10.1021/acs.orglett.1c01762 34251821
    [Google Scholar]
  88. Wang X. Fu J.P. Xie J.X. Teng Q.H. Tang H.T. Pan Y.M. Palladium-catalyzed synthesis of 5-amino-1,2,4-oxadiazoles via isocyanide insertion. Org. Biomol. Chem. 2020 18 26 4936 4940 10.1039/D0OB01092H 32583841
    [Google Scholar]
  89. Collet J.W. Roose T.R. Weijers B. Maes B.U.W. Ruijter E. Orru R.V.A. Recent advances in palladium-catalyzed isocyanide insertions. Molecules 2020 25 21 4906 10.3390/molecules25214906 33114013
    [Google Scholar]
  90. Stephan M. Panther J. Wilbert F. Ozog P. Muller T.J.J. 3-Aryl propenals and propenones by heck reaction of aryl bromides and acrolein or enones - Application to consecutive three-component and pseudo four-component pyrazole syntheses. Eur. J. Org. Chem. 2020 10.1002/ejoc.202000066
    [Google Scholar]
  91. Thirukovela N.S. Balaboina R. Botla V. Vadde R. Jonnalagadda S.B. Vasam C.S. One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization. Catal. Sci. Technol. 2019 9 22 6471 6481 10.1039/C9CY01335K
    [Google Scholar]
  92. Mandal S. Bera T. Dubey G. Saha J. Laha J.K. Uses of K2S2O8 in metal-catalyzed and metal-free oxidative transformations. ACS Catal. 2018 8 6 5085 5144 10.1021/acscatal.8b00743
    [Google Scholar]
  93. Dai L. Yu S. Shao Y. Li R. Chen Z. Lv N. Chen J. Palladium-catalyzed C-H activation of simple arenes and cascade reaction with nitriles: Access to 2,4,5-trisubstituted oxazoles. Chem. Commun. 2021 57 11 1376 1379 10.1039/D0CC07547G 33433549
    [Google Scholar]
  94. Yao X. Qi L. Li R. Zhen Q. Liu J. Zhao Z. Shao Y. Hu M. Chen J. Palladium-catalyzed cascade reactions of δ-ketonitriles with arylboronic acids: Synthesis of pyridines. ACS Comb. Sci. 2020 22 3 114 119 10.1021/acscombsci.9b00198 32049476
    [Google Scholar]
  95. Rieckhoff S. Hellmuth T. Peters R. Regioselective Pd-catalyzed synthesis of 2,3,6-trisubstituted pyridines from isoxazolinones. J. Org. Chem. 2015 80 13 6822 6830 10.1021/acs.joc.5b01065 26101943
    [Google Scholar]
  96. Meng J. Liu H. Wu Z. Zhang W. Palladium catalyzed aerobic oxidative amination of alkenes. Asian J. Org. Chem. 2023 12 6 202300172 10.1002/ajoc.202300172
    [Google Scholar]
  97. Montgomery T.D. Rawal V.H. Palladium-catalyzed modular synthesis of substituted piperazines and related nitrogen heterocycles. Org. Lett. 2016 18 4 740 743 10.1021/acs.orglett.5b03708 26824482
    [Google Scholar]
  98. Magriotis P.A. Recent progress toward the asymmetric synthesis of carbon-substituted piperazine pharmacophores and oxidative related heterocycles. RSC Med. Chem. 2020 11 7 745 759 10.1039/D0MD00053A 33479672
    [Google Scholar]
  99. Faltracco M. Cotogno S. Vande Velde C.M.L. Ruijter E. Catalytic asymmetric synthesis of diketopiperazines by intramolecular Tsuji-Trost allylation. J. Org. Chem. 2019 84 18 12058 12070 10.1021/acs.joc.9b01994 31446758
    [Google Scholar]
  100. Yao L.F. Wang Y. Huang K.W. Synthesis of morpholine or piperazine derivatives through gold-catalyzed cyclization reactions of alkynylamines or alkynylalcohols. Org. Chem. Front. 2015 2 6 721 725 10.1039/C5QO00060B
    [Google Scholar]
  101. Pospelov E.V. Boyko Y.D. Ioffe S.L. Sukhorukov A.Y. Synthesis of bis (β‐Oximinoalkyl) malonates and their catalytic reductive cyclization to piperidines. Adv. Synth. Catal. 2022 364 15 2557 2564 10.1002/adsc.202200424
    [Google Scholar]
  102. Pospelov E.V. Sukhorukov A.Y. Building up a Piperazine ring from a primary amino group via catalytic reductive cyclization of Dioximes. Int. J. Mol. Sci. 2023 24 14 11794 10.3390/ijms241411794 37511552
    [Google Scholar]
  103. Poly S.S. Hashiguchi Y. Sultana A. Nakamura I. Shimizu K. Yasumura S. Fujitani T. Flow reactor approach for the facile and continuous synthesis of efficient Pd@Pt core-shell nanoparticles for acceptorless dehydrogenative synthesis of pyrimidines from alcohols and amidines. Appl. Catal. A Gen. 2021 619 118158 10.1016/j.apcata.2021.118158
    [Google Scholar]
  104. Buron F. Mérour J.Y. Akssira M. Guillaumet G. Routier S. Recent advances in the chemistry and biology of pyridopyrimidines. Eur. J. Med. Chem. 2015 95 76 95 10.1016/j.ejmech.2015.03.029 25794791
    [Google Scholar]
  105. Riadi Y. UV light mediated palladium-catalyzed synthesis of 2-substituedpyrido[2,3- d]pyrimidines. Polycycl. Aromat. Compd. 2021 41 6 1141 1146 10.1080/10406638.2019.1665554
    [Google Scholar]
  106. Reddy Kotla S.K. Vandavasi J.K. Wang J.J. Parang K. Tiwari R.K. Palladium-catalyzed intramolecular cross-dehydrogenative coupling: Synthesis of fused imidazo [1, 2-a] pyrimidines and pyrazolo [1, 5-a] pyrimidines. ACS Omega 2017 2 1 11 19 10.1021/acsomega.6b00417 31457205
    [Google Scholar]
  107. El-Remaily M.A.E.A.A.A. Soliman A.M.M. Khalifa M.E. El-Metwaly N.M. Alsoliemy A. El-Dabea T. Abu-Dief A.M. Rapidly, highly yielded and green synthesis of dihydrotetrazolo[1,5‐ a]pyrimidine derivatives in aqueous media using recoverable Pd (II) thiazole catalyst accelerated by ultrasonic: Computational studies. Appl. Organomet. Chem. 2022 36 2 6320 10.1002/aoc.6320
    [Google Scholar]
/content/journals/coc/10.2174/0113852728404183251203015241
Loading
/content/journals/coc/10.2174/0113852728404183251203015241
Loading

Data & Media loading...


  • Article Type:
    Review Article
Keywords: heterocycle compound ; diabetes ; catalyst ; heterocyclic ; nanoparticles ; Palladium
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test