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Heterocycles via Cross Dehydrogenative Coupling pp 35–75Cite as

Functionalization of Aromatic N-Heterocycles via C(sp2)–H/C(sp2)–H CDC Reactions

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Abstract

This review is devoted to dehydrogenative C(sp2)–C(sp2) cross-coupling reactions. In the review we discussed the reactions of aromatic N-heterocycles with such reagents as amides and aldehydes, alkenes, aromatic and heterocyclic compounds with the formation of the corresponding C–H/C–H coupling products. The review is focused on mechanism as well as scope and limitations of dehydrogenative cross-coupling reactions.

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References

  1. Fanta PE (1974) The Ullmann synthesis of biaryls. Synthesis 1974:9–21

    Article  Google Scholar 

  2. Colacot TJ (2015) New trends in cross-coupling: theory and applications. The Royal Society of Chemistry, Cambridge

    Google Scholar 

  3. Minisci F (1976) Recent aspects of homolytic aromatic substitutions. In: Minisci F, Hendrickson JB, Wentrup C (eds) Synthetic and mechanistic organic chemistry. Springer, Berlin, pp 1–48

    Chapter  Google Scholar 

  4. Citterio A, Gentile A, Minisci F, Serravalle M, Ventura S (1984) Polar effects in free-radical reactions. Carbamoylation and α-N-amidoalkylation of heteroaromatic bases by amides and hydroxylamine-O-sulfonic acid. J Org Chem 49:3364–3367

    Article  CAS  Google Scholar 

  5. Citterio A, Gentile A, Minisci F, Serravalle M, Ventura S (1983) Redox-chain decomposition of hydroxylamine-O-sulphonic acid. A novel general source of nucleophilic radicals for the functionalization of heteroaromatic bases. J Chem Soc Chem Commun (16):916–917

    Google Scholar 

  6. Yao B, Deng C-L, Liu Y, Tang R-Y, Zhang X-G, Li J-H (2015) Palladium-catalyzed oxidative carbamoylation of isoquinoline N-oxides with formylamides by means of dual C-H oxidative coupling. Chem Commun 51:4097–4100

    Article  CAS  Google Scholar 

  7. Han W, Jin F, Zhao Q, Du H, Yao L (2016) Acid-free silver-catalyzed cross-dehydrogenative carbamoylation of pyridines with formamides. Synlett 27:1854–1859

    Article  CAS  Google Scholar 

  8. Mete TB, Singh A, Bhat RG (2017) Transition-metal-free synthesis of primary to tertiary carboxamides: a quick access to prodrug-pyrazinecarboxamide. Tetrahedron Lett 58:4709–4712

    Article  CAS  Google Scholar 

  9. Edwards AC, Geist A, Müllich U, Sharrad CA, Pritchard RG, Whitehead RC, Harwood LM (2017) Transition metal-free, visible-light mediated synthesis of 1,10-phenanthroline derived ligand systems. Chem Commun 53:8160–8163

    Article  CAS  Google Scholar 

  10. Lewis FW, Harwood LM, Hudson MJ, Drew MGB, Hubscher-Bruder V, Videva V, Arnaud-Neu F, Stamberg K, Vyas S (2013) BTBPs versus BTPhens: some reasons for their differences in properties concerning the partitioning of minor actinides and the advantages of BTPhens. Inorg Chem 52:4993–5005

    Article  CAS  PubMed  Google Scholar 

  11. Higginson MA, Kyle ND, Marsden OJ, Thompson P, Livens FR, Heath SL (2015) Synthesis of functionalised BTPhen derivatives—effects on solubility and americium extraction. Dalton Trans 44:16547–16552

    Article  CAS  PubMed  Google Scholar 

  12. He T, Li H, Li P, Wang L (2011) Direct amidation of azoles with formamides via metal-free C-H activation in the presence of tert-butyl perbenzoate. Chem Commun 47:8946–8948

    Article  CAS  Google Scholar 

  13. Zhang Y, Teuscher KB, Ji H (2016) Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction. Chem Sci 7:2111–2118

    Article  CAS  PubMed  Google Scholar 

  14. Matcha K, Antonchick AP (2013) Metal-free cross-dehydrogenative coupling of heterocycles with aldehydes. Angew Chem Int Ed 52:2082–2086

    Article  CAS  Google Scholar 

  15. Cheng P, Qing Z, Liu S, Liu W, Xie H, Zeng J (2014) Regiospecific Minisci acylation of phenanthridine via thermolysis or photolysis. Tetrahedron Lett 55:6647–6651

    Article  CAS  Google Scholar 

  16. Siddaraju Y, Lamani M, Prabhu KR (2014) A transition metal-free Minisci reaction: acylation of isoquinolines, quinolines, and quinoxaline. J Org Chem 79:3856–3865

    Article  CAS  PubMed  Google Scholar 

  17. Chen J, Wan M, Hua J, Sun Y, Lv Z, Li W, Liu L (2015) TBHP/TFA mediated oxidative cross-dehydrogenative coupling of N-heterocycles with aldehydes. Org Biomol Chem 13:11561–11566

    Article  CAS  PubMed  Google Scholar 

  18. Siddaraju Y, Prabhu KR (2016) Transition metal-free Minisci reaction promoted by NCS, and TBHP: acylation of heteroarenes. Tetrahedron 72:959–967

    Article  CAS  Google Scholar 

  19. Kianmehr E, Kazemi S, Foroumadi A (2014) Palladium-catalyzed oxidative C-H bond coupling of indoles and benzaldehydes: a new approach to the synthesis of 3-benzoylindoles. Tetrahedron 70:349–354

    Article  CAS  Google Scholar 

  20. Shakoor SMA, Agarwal DS, Kumar A, Sakhuja R (2016) Copper catalyzed direct aerobic double-oxidative cross-dehydrogenative coupling of imidazoheterocycles with aryl acetaldehydes: an articulate approach for dicarbonylation at C-3 position. Tetrahedron 72:645–652

    Article  CAS  Google Scholar 

  21. Samanta S, Mondal S, Santra S, Kibriya G, Hajra A (2016) FeCl3-catalyzed cross-dehydrogenative coupling between imidazoheterocycles and oxoaldehydes. J Org Chem 81:10088–10093

    Article  CAS  PubMed  Google Scholar 

  22. Yeung CS, Dong VM (2011) Catalytic dehydrogenative cross-coupling: forming carbon−carbon bonds by oxidizing two carbon−hydrogen bonds. Chem Rev 111:1215–1292

    Article  CAS  PubMed  Google Scholar 

  23. Ferreira EM, Zhang H, Stoltz BM (2009) Oxidative heck‐type reactions (Fujiwara–Moritani reactions). In: The Mizoroki–Heck reaction. Wiley-Blackwell, Hoboken, pp 345–382

    Google Scholar 

  24. Li JJ (2009) Heck reaction. In: Li JJ (ed) Name reactions: a collection of detailed mechanisms and synthetic applications. Springer, Berlin, pp 277–280

    Chapter  Google Scholar 

  25. Hu H, Liu Y, Zhong H, Zhu Y, Wang C, Ji M (2012) Heck-type cross-dehydrogenative coupling reactions of indolizines at the 3-position with electron-deficient alkenes through palladium-catalyzed C–H activation. Chem Asian J 7:884–888

    Article  CAS  PubMed  Google Scholar 

  26. Koubachi J, Berteina-Raboin S, Mouaddib A, Guillaumet G (2009) Pd/Cu-catalyzed oxidative C-H alkenylation of imidazo[1,2-a]pyridines. Synthesis 2009:271–276

    Article  CAS  Google Scholar 

  27. Zhan H, Zhao L, Li N, Chen L, Liu J, Liao J, Cao H (2014) Ruthenium-catalyzed direct C-3 oxidative olefination of imidazo[1,2-a]pyridines. RSC Adv 4:32013–32016

    Article  CAS  Google Scholar 

  28. Ghosh M, Naskar A, Mitra S, Hajra A (2015) Palladium-catalyzed α-selective alkenylation of imidazo[1,2-a]pyridines through aerobic cross-dehydrogenative coupling reaction. Eur J Org Chem 2015:715–718

    Article  CAS  Google Scholar 

  29. Yang Y, Cheng K, Zhang Y (2009) Highly regioselective palladium-catalyzed oxidative coupling of indolizines and vinylarenes via C−H bond cleavage. Org Lett 11:5606–5609

    Article  CAS  PubMed  Google Scholar 

  30. Lee W-C, Wang T-H, Ong T-G (2014) Ligand promoted Pd-catalyzed dehydrogenative alkenylation of hetereoarenes. Chem Commun 50:3671–3673

    Article  CAS  Google Scholar 

  31. Zhang Z, Zheng Y, Sun Z, Dai Z, Tang Z, Ma J, Ma C (2017) Direct olefination of fluorinated quinoxalines via cross-dehydrogenative coupling reactions: a new near-infrared probe for mitochondria. Adv Synth Catal 359:2259–2268

    Article  CAS  Google Scholar 

  32. Liu W, Wang S, Zhan H, Lin J, He P, Jiang Y (2014) Highly regioselective palladium-catalyzed direct alkenylation of thiazolo[3,2-b]-1,2,4-triazoles via CH activation. Tetrahedron Lett 55:3549–3552

    Article  CAS  Google Scholar 

  33. Beck EM, Grimster NP, Hatley R, Gaunt MJ (2006) Mild aerobic oxidative palladium (II) catalyzed C−H bond functionalization: regioselective and switchable C−H alkenylation and annulation of pyrroles. J Am Chem Soc 128:2528–2529

    Article  CAS  PubMed  Google Scholar 

  34. Su Y, Zhou H, Chen J, Xu J, Wu X, Lin A, Yao H (2014) Solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates: application to the total synthesis of (±)-rhazinilam. Org Lett 16:4884–4887

    Article  CAS  PubMed  Google Scholar 

  35. Bugaut X, Glorius F (2011) Palladium-catalyzed selective dehydrogenative cross-couplings of heteroarenes. Angew Chem Int Ed 50:7479–7481

    Article  CAS  Google Scholar 

  36. Hirano K, Miura M (2015) Copper-mediated intermolecular C–H/C–H and C–H/N–H couplings via aromatic C–H cleavage. C-H bond activation and catalytic functionalization II. Springer, Cham, pp 47–65

    Chapter  Google Scholar 

  37. Varun BV, Dhineshkumar J, Bettadapur KR, Siddaraju Y, Alagiri K, Prabhu KR (2017) Recent advancements in dehydrogenative cross coupling reactions for CC bond formation. Tetrahedron Lett 58:803–824

    Article  CAS  Google Scholar 

  38. Yang Y, Lan J, You J (2017) Oxidative C-H/C–H coupling reactions between two (hetero)arenes. Chem Rev 117:8787–8863

    Article  CAS  PubMed  Google Scholar 

  39. Charushin V, Chupakhin O (2018) Metal-free C–H functionalization of aromatic compounds through the action of nucleophilic reagents. SpringerLink. https://link.springer.com/chapter/10.1007/7081_2013_119. Accessed 21 Sept 2018

  40. Mao Z, Wang Z, Xu Z, Huang F, Yu Z, Wang R (2012) Copper(II)-mediated dehydrogenative cross-coupling of heteroarenes. Org Lett 14:3854–3857

    Article  CAS  PubMed  Google Scholar 

  41. Qin X, Feng B, Dong J, Li X, Xue Y, Lan J, You J (2012) Copper(II)-catalyzed dehydrogenative cross-coupling between two azoles. J Org Chem 77:7677–7683

    Article  CAS  PubMed  Google Scholar 

  42. Fan S, Chen Z, Zhang X (2012) Copper-catalyzed dehydrogenative cross-coupling of benzothiazoles with thiazoles and polyfluoroarene. Org Lett 14:4950–4953

    Article  CAS  PubMed  Google Scholar 

  43. Yang S-W, Su Y-X, Sun L-P (2014) Palladium-catalyzed oxidative C-H/C–H cross-couplings of thiazolo[5,4-d]pyrimidine with aromatic (hetero)cycles. Tetrahedron 70:3730–3734

    Article  CAS  Google Scholar 

  44. Kuhl N, Hopkinson MN, Glorius F (2012) Selective rhodium(III)-catalyzed cross-dehydrogenative coupling of furan and thiophene derivatives. Angew Chem Int Ed 51:8230–8234

    Article  CAS  Google Scholar 

  45. Li Y, Wang W-H, Yang S-D, Li B-J, Feng C, Shi Z-J (2010) Oxidative dimerization of N-protected and free indole derivatives toward 3,3′-biindoles via Pd-catalyzed direct C-H transformations. Chem Commun 46:4553–4555

    Article  CAS  Google Scholar 

  46. Total synthesis of 5,5′,6,6′-tetrahydroxy-3,3′-biindolyl, the proposed structure of a potent antioxidant found in beetroot (Beta vulgaris)—ScienceDirect. https://www.sciencedirect.com/science/article/pii/S0040402004002996. Accessed 9 Nov 2018

  47. Xia J-B, Wang X-Q, You S-L (2009) Synthesis of biindolizines through highly regioselective palladium-catalyzed C−H functionalization. J Org Chem 74:456–458

    Article  CAS  PubMed  Google Scholar 

  48. Lei S, Cao H, Chen L, Liu J, Cai H, Tan J (2015) Regioselective oxidative homocoupling reaction: an efficient copper-catalyzed synthesis of biimidazo[1,2-a]pyridines. Adv Synth Catal 357:3109–3114

    Article  CAS  Google Scholar 

  49. Nishino M, Hirano K, Satoh T, Miura M (2012) Copper-mediated and copper-catalyzed cross-coupling of indoles and 1,3-azoles: double C-H activation. Angew Chem Int Ed 51:6993–6997

    Article  CAS  Google Scholar 

  50. Le J, Gao Y, Ding Y, Jiang C (2016) Cu-mediated C2-dehydrogenative homocoupling of indoles via C-H activation assisted by a removable N-pyrimidyl group. Tetrahedron Lett 57:1728–1731

    Article  CAS  Google Scholar 

  51. Qin X, Liu H, Qin D, Wu Q, You J, Zhao D, Guo Q, Huang X, Lan J (2013) Chelation-assisted Rh(III)-catalyzed C2-selective oxidative C-H/C–H cross-coupling of indoles/pyrroles with heteroarenes. Chem Sci 4:1964–1969

    Article  CAS  Google Scholar 

  52. Reddy VP, Qiu R, Iwasaki T, Kambe N (2013) Rhodium-catalyzed intermolecular oxidative cross-coupling of (hetero)arenes with chalcogenophenes. Org Lett 15:1290–1293

    Article  CAS  PubMed  Google Scholar 

  53. Tripathi KN, Ray D, Singh RP (2017) Pd-Catalyzed regioselective intramolecular dehydrogenative C-5 cross coupling in an N-substituted pyrrole-azole system. Org Biomol Chem 15:10082–10086

    Article  CAS  PubMed  Google Scholar 

  54. Tripathi KN, Ray D, Singh RP (2017) Synthesis of pyrrole-annulated heterocycles through copper-catalyzed site-selective dehydrogenative cross-coupling. Eur J Org Chem 2017:5809–5813

    Article  CAS  Google Scholar 

  55. Ray D, Manikandan T, Roy A, Tripathi KN, Singh RP (2015) Ligand-promoted intramolecular dehydrogenative cross-coupling using a Cu catalyst: direct access to polycyclic heteroarenes. Chem Commun 51:7065–7068

    Article  CAS  Google Scholar 

  56. Mantenuto S, Ciccolini C, Lucarini S, Piersanti G, Favi G, Mantellini F (2017) Palladium(II)-catalyzed intramolecular oxidative C-H/C–H cross-coupling reaction of C3, N-linked biheterocycles: rapid access to polycyclic nitrogen heterocycles. Org Lett 19:608–611

    Article  CAS  PubMed  Google Scholar 

  57. Bharathimohan K, Ponpandian T, Ahamed AJ, Bhuvanesh N (2014) Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles. Beilstein J Org Chem 10:3031–3037

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  58. Wang Z, Li B, Zhang X, Fan X (2016) One-pot cascade reactions leading to pyrido[2′,1′:2,3]imidazo[4,5-c][1,2,3]triazolo[1,5-a]quinolines under bimetallic relay catalysis with air as the oxidant. J Org Chem 81:6357–6363

    Article  CAS  PubMed  Google Scholar 

  59. Pericherla K, Khedar P, Khungar B, Kumar A (2013) One-pot sequential C-N coupling and cross dehydrogenative couplings: synthesis of novel azole fused imidazo[1,2-a]pyridines. Chem Commun 49:2924–2926

    Article  CAS  Google Scholar 

  60. Wu G, Zhou J, Zhang M, Hu P, Su W (2012) Palladium-catalyzed direct arylation of benzoxazoles with unactivated simple arenes. Chem Commun 48:8964–8966

    Article  CAS  Google Scholar 

  61. Malakar CC, Schmidt D, Conrad J, Beifuss U (2011) Double C−H activation: the palladium-catalyzed direct C-arylation of xanthines with arenes. Org Lett 13:1378–1381

    Article  CAS  PubMed  Google Scholar 

  62. Li Z, Ma L, Xu J, Kong L, Wu X, Yao H (2012) Pd(II)-catalyzed direct C5-arylation of azole-4-carboxylates through double C-H bond cleavage. Chem Commun 48:3763–3765

    Article  CAS  Google Scholar 

  63. Wang S, Liu W, Cen J, Liao J, Huang J, Zhan H (2014) Pd-catalyzed oxidative cross-coupling of imidazo[1,2-a]pyridine with arenes. Tetrahedron Lett 55:1589–1592

    Article  CAS  Google Scholar 

  64. Banerji B, Chatterjee S, Chandrasekhar K, Bera S, Majumder L, Prodhan C, Chaudhuri K (2017) Expedient synthesis of a phenanthro-imidazo-pyridine fused heteropolynuclear framework via CDC coupling: a new class of luminophores. Org Biomol Chem 15:4130–4134

    Article  CAS  PubMed  Google Scholar 

  65. Pereira KC, Porter AL, DeBoef B (2014) Intramolecular arylation of benzimidazoles via Pd(II)/Cu(I) catalyzed cross-dehydrogenative coupling. Tetrahedron Lett 55:1729–1732

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  66. Dong J, Long Z, Song F, Wu N, Guo Q, Lan J, You J (2013) Rhodium or ruthenium-catalyzed oxidative C-H/C-H cross-coupling: direct access to extended π-conjugated systems. Angew Chem Int Ed 52:580–584

    Article  CAS  Google Scholar 

  67. Liu H, Xu H, Yuan Y (2014) Rhodium-catalyzed direct oxidative cross-coupling of 2-aryl pyridine with benzothiazoles. Tetrahedron 70:6474–6481

    Article  CAS  Google Scholar 

  68. Kitahara M, Umeda N, Hirano K, Satoh T, Miura M (2011) copper-mediated intermolecular direct biaryl coupling. J Am Chem Soc 133:2160–2162

    Article  CAS  PubMed  Google Scholar 

  69. Odani R, Hirano K, Satoh T, Miura M (2013) Copper-mediated dehydrogenative biaryl coupling of naphthylamines and 1,3-azoles. J Org Chem 78:11045–11052

    Article  CAS  PubMed  Google Scholar 

  70. Nishino M, Hirano K, Satoh T, Miura M (2013) Copper-mediated C-H/C-H biaryl coupling of benzoic acid derivatives and 1,3-azoles. Angew Chem Int Ed 52:4457–4461

    Article  CAS  Google Scholar 

  71. Shang Y, Jie X, Zhao H, Hu P, Su W (2014) Rh(III)-catalyzed amide-directed cross-dehydrogenative heteroarylation of pyridines. Org Lett 16:416–419

    Article  CAS  PubMed  Google Scholar 

  72. Deng H, Li H, Wang L (2016) Ortho-heteroarylation of azobenzenes by Rh-catalyzed cross-dehydrogenative coupling: an approach to conjugated biaryls. Org Lett 18:3110–3113

    Article  CAS  PubMed  Google Scholar 

  73. Kianmehr E, Fardpour M, Kharat AN (2017) Palladium-catalyzed chemo- and regioselective oxidative cross-dehydrogenative coupling of acetanilides with benzothiazole. Eur J Org Chem 2017:3017–3021

    Article  CAS  Google Scholar 

  74. Bhunia SK, Polley A, Natarajan R, Jana R (2015) Through-space 1,4-palladium migration and 1,2-aryl shift: direct access to dibenzo[a,c]carbazoles through a triple C–H functionalization cascade. Chem Eur J 21:16786–16791

    Article  CAS  PubMed  Google Scholar 

  75. Zou L-H, Mottweiler J, Priebbenow DL, Wang J, Stubenrauch JA, Bolm C (2013) Mild copper-mediated direct oxidative cross-coupling of 1,3,4-oxadiazoles with polyfluoroarenes by using dioxygen as oxidant. Chem Eur J 19:3302–3305

    Article  CAS  PubMed  Google Scholar 

  76. Liu S, Tzschucke CC (2016) Palladium-catalyzed regioselective dehydrogenative C-H/C–H cross-coupling of pyrroles and pyridine N-oxides. Eur J Org Chem 2016:3509–3513

    Article  CAS  Google Scholar 

  77. Suresh R, Muthusubramanian S, Senthilkumaran R (2014) Regioselective cross-dehydrogenative coupling of indole-2-carboxylic acids and pyridine-N-oxides followed by protodecarboxylation. Synlett 25:2064–2066

    Article  CAS  Google Scholar 

  78. Gong X, Song G, Zhang H, Li X (2011) Palladium-catalyzed oxidative cross-coupling between pyridine N-oxides and indoles. Org Lett 13:1766–1769

    Article  CAS  PubMed  Google Scholar 

  79. Willis NJ, Smith JM (2014) An operationally simple, palladium catalysed dehydrogenative cross-coupling reaction of pyridine N-oxides and thiazoles “on water”. RSC Adv 4:11059–11063

    Article  CAS  Google Scholar 

  80. Fu X-P, Xuan Q-Q, Liu L, Wang D, Chen Y-J, Li C-J (2013) Dual C-H activations of electron-deficient heteroarenes: palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides. Tetrahedron 69:4436–4444

    Article  CAS  Google Scholar 

  81. Kianmehr E, Faghih N, Khan KM (2015) Palladium-catalyzed regioselective benzylation-annulation of pyridine N-oxides with toluene derivatives via multiple C-H bond activations: benzylation versus arylation. Org Lett 17:414–417

    Article  CAS  PubMed  Google Scholar 

  82. Kianmehr E, Rezaeefard M, Khalkhali MR, Khan KM (2014) Pd-catalyzed dehydrogenative cross-coupling of pyridine-N-oxides with uracils. RSC Adv 4:13764–13767

    Article  CAS  Google Scholar 

  83. Odani R, Hirano K, Satoh T, Miura M (2014) Copper-mediated C6-selective dehydrogenative heteroarylation of 2-pyridones with 1,3-azoles. Angew Chem Int Ed 53:10784–10788

    Article  CAS  Google Scholar 

  84. Yamada S, Murakami K, Itami K (2016) Regiodivergent cross-dehydrogenative coupling of pyridines and benzoxazoles: discovery of organic halides as regio-switching oxidants. Org Lett 18:2415–2418

    Article  CAS  PubMed  Google Scholar 

  85. Hong F, Chen Y, Lu B, Cheng J (2016) One-pot assembly of fused heterocycles via oxidative palladium-catalyzed cyclization of arylols and iodoarenes. Adv Synth Catal 358:353–357

    Article  CAS  Google Scholar 

  86. Cheng C, Chen W-W, Xu B, Xu M-H (2016) Access to indole-fused polyheterocycles via Pd-catalyzed base-free intramolecular cross dehydrogenative coupling. J Org Chem 81:11501–11507

    Article  CAS  PubMed  Google Scholar 

  87. Ren X, Wen P, Shi X, Wang Y, Li J, Yang S, Yan H, Huang G (2013) Palladium-catalyzed C-2 selective arylation of quinolines. Org Lett 15:5194–5197

    Article  CAS  PubMed  Google Scholar 

  88. Chupakhin ON, Shchepochkin AV, Charushin VN (2017) Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C-C coupling reactions. Green Chem 19:2931–2935

    Article  CAS  Google Scholar 

  89. Utepova IA, Trestsova MA, Chupakhin ON, Charushin VN, Rempel AA (2015) Aerobic oxidative C-H/C–H coupling of azaaromatics with indoles and pyrroles in the presence of TiO2 as a photocatalyst. Green Chem 17:4401–4410

    Article  CAS  Google Scholar 

  90. Han Y-Y, Wu Z-J, Zhang X-M, Yuan W-C (2010) An efficient synthesis of 3-(indol-3-yl)quinoxaline-2-ones with TfOH-catalyzed Friedel-Crafts type coupling reaction in air. Tetrahedron Lett 51:2023–2028

    Article  CAS  Google Scholar 

  91. Noikham M, Kittikool T, Yotphan S (2018) Iodine-catalyzed oxidative cross-dehydrogenative coupling of quinoxalinones and indoles: synthesis of 3-(indol-2-yl)quinoxalin-2-one under mild and ambient conditions. Synthesis 50:2337–2346

    Article  CAS  Google Scholar 

  92. Azev YA, Ermakova OS, Berseneva VS, Bakulev VA, Ezhikova MA, Kodess MI (2017) Synthesis of fluoroquinoxalin-2(1H)-one derivatives containing substituents in the pyrazine and benzene fragments. Russ J Org Chem 53:90–95

    Article  CAS  Google Scholar 

  93. Chupakhin ON, Egorov IN, Rusinov VL, Slepukhin PA (2010) Asymmetric induction in the reactions of azinones with C-nucleophiles. Russ Chem Bull 59:991–1001

    Article  CAS  Google Scholar 

  94. Khalymbadzha IA, Fatykhov RF, Chupakhin ON, Charushin VN, Tseitler TA, Sharapov AD, Inytina AK, Kartsev VG (2018) Transition-metal-free C-C coupling of 5,7-dihydroxybenzopyrones with quinoxalones and pteridinones. Synthesis 50:2423–2431

    Article  CAS  Google Scholar 

  95. Borovlev IV, Demidov OP, Borovlev II, Saigakova NA (2013) 1,3,7-triazapyrene: the first case of hetarylation of benzene and its analogs. Chem Heterocycl Compd 49:952–954

    Article  CAS  Google Scholar 

  96. Borovlev IV, Demidov OP, Saigakova NA (2013) SNH arylation of 1,3,7-triazapyrenes in acidic aqueous solution. Chem Heterocycl Compd 49:618–623

    Article  CAS  Google Scholar 

  97. Khalymbadzha IA, Chupakhin ON, Fatykhov RF, Charushin VN, Schepochkin AV, Kartsev VG (2016) Transition-metal-free cross-dehydrogenative coupling of triazines with 5,7-dihydroxycoumarins. Synlett 27:2606–2610

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by the Russian Science Foundation (project #19-73-10144).

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Authors and Affiliations

  1. Ural Federal University, Mira, 19, 620002, Ekaterinburg, Russian Federation

    Igor A. Khalymbadzha, Ramil F. Fatykhov & Oleg N. Chupakhin

  2. I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya/Akademicheskaya, 22/20, 620219, Ekaterinburg, Russian Federation

    Igor A. Khalymbadzha & Oleg N. Chupakhin

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  1. Igor A. Khalymbadzha
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  2. Ramil F. Fatykhov
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  3. Oleg N. Chupakhin
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Correspondence to Igor A. Khalymbadzha .

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Editors and Affiliations

  1. National Institute of Pharmaceutical Education and Research, Guwahati, Assam, India

    Ananya Srivastava

  2. Indian Institute of Technology Guwahati, Guwahati, Assam, India

    Chandan K. Jana

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Khalymbadzha, I.A., Fatykhov, R.F., Chupakhin, O.N. (2019). Functionalization of Aromatic N-Heterocycles via C(sp2)–H/C(sp2)–H CDC Reactions. In: Srivastava, A., Jana, C. (eds) Heterocycles via Cross Dehydrogenative Coupling. Springer, Singapore. https://doi.org/10.1007/978-981-13-9144-6_2

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