Skip to content
2000
Volume 22, Issue 8
  • ISSN: 1570-1786
  • E-ISSN: 1875-6255

Abstract

Over the past decades, 2,2’-bipyridines and their derivatives have significantly contributed to the field of advanced materials, synthesis, and catalysis. In particular, the structural ability of bipyridines to accommodate numerous types of functional groups with varying electronic and steric properties resulted in their diverse applications. In this regard, developing novel and cost-effective preparative methodologies for 2,2’-bipyridines having various substituents has always been a popular area of research. Starting from pyridine derivatives, the simplest route to these molecules includes homo-, hetero-, and cross-coupling reactions. This review concentrated on transition metal-mediated one-step procedures for 2,2’-bipyridines from inexpensive and abundant starting materials, specifically, pyridines and 2-halopyridines. Although this report focuses on self-coupling techniques, convenient hetero-coupling methods are included. Special attention is given to the substrate scope details of the existing methodologies.

Loading

Article metrics loading...

/content/journals/loc/10.2174/0115701786350613250118104808
2025-02-12
2025-09-08
Loading full text...

Full text loading...

References

  1. (a KaesC. KatzA. HosseiniM.W. Chem. Rev.2000100103553359010.1021/cr990376z11749322
    [Google Scholar]
  2. (b LiuB. YuW.L. PeiJ. LiuS.Y. LaiY.H. HuangW. Macromolecules200134237932794010.1021/ma0106651
    [Google Scholar]
  3. (c BalzaniV. JurisA. Coord. Chem. Rev.200121119711510.1016/S0010‑8545(00)00274‑5
    [Google Scholar]
  4. (d HassanJ. SévignonM. GozziC. SchulzE. LemaireM. Chem. Rev.200210251359147010.1021/cr000664r11996540
    [Google Scholar]
  5. (e RichardJ. JosephJ. WangC. CiesielskiA. WeissJ. SamorìP. MamaneV. WytkoJ.A. J. Org. Chem.20218643356336610.1021/acs.joc.0c0270833539085
    [Google Scholar]
  6. (a ConstableE.C. HousecroftC.E. Molecules20192421395110.3390/molecules2421395131683694
    [Google Scholar]
  7. (b ChelucciG. ThummelR.P. Chem. Rev.200210293129317010.1021/cr010191412222984
    [Google Scholar]
  8. (c HapkeM. BrandtL. LützenA. Chem. Soc. Rev.200837122782279710.1039/b810973g19020687
    [Google Scholar]
  9. (d OlivaresA.M. WeixD.J. J. Am. Chem. Soc.201814072446244910.1021/jacs.7b1360129420028
    [Google Scholar]
  10. (a WangS. MaP. ShaikS. ChenH. J. Am. Chem. Soc.202214432146071461310.1021/jacs.2c0383535925767
    [Google Scholar]
  11. (b MaityB. ScottT.R. StroscioG.D. GagliardiL. CavalloL. ACS Catal.20221221132151322410.1021/acscatal.2c04284
    [Google Scholar]
  12. (c DurinG. LeeM.Y. PoganyM.A. WeyhermüllerT. KaefferN. LeitnerW. J. Am. Chem. Soc.202314531171031711110.1021/jacs.3c0334037490541
    [Google Scholar]
  13. (d PiszelP.E. OrzolekB.J. OlszewskiA.K. RotellaM.E. SpiewakA.M. KozlowskiM.C. WeixD.J. J. Am. Chem. Soc.2023145158517852810.1021/jacs.3c00618
    [Google Scholar]
  14. (a RubtsovA.E. MalkovA.V. Synthesis202153152559256910.1055/s‑0040‑1706030
    [Google Scholar]
  15. (b HaguiW. PeriasamyK. SouléJ.F. Eur. J. Org. Chem.20212021395388540210.1002/ejoc.202100806
    [Google Scholar]
  16. (c YamanoiY. Molecules202429357610.3390/molecules2903057638338319
    [Google Scholar]
  17. (d NairS.B. AthalyeA.S. PanphaliaM. ParikhF.R. Hemoglobin202246526927110.1080/03630269.2022.212249736120956
    [Google Scholar]
  18. (a BlauF. Berg. Huettenmaenn. Monatsh18882110771082
    [Google Scholar]
  19. (b WeidelH. Ber. Dtsch. Chem. Ges.18791221989201210.1002/cber.187901202207
    [Google Scholar]
  20. (a AndersonT. Justus Liebigs Ann. Chem.1870154327028610.1002/jlac.18701540303
    [Google Scholar]
  21. (b AndersonT. J. Chem. Soc.186922040641710.1039/JS8692200406
    [Google Scholar]
  22. (c EmmertB. Ber. Dtsch. Chem. Ges.1917501313510.1002/cber.19170500107
    [Google Scholar]
  23. (d EmmertB. Ber. Dtsch. Chem. Ges.19144732598260110.1002/cber.19140470335
    [Google Scholar]
  24. (e EmmertB. Ber. Dtsch. Chem. Ges.19164911060106210.1002/cber.191604901113
    [Google Scholar]
  25. (f EmmertB. BuchertR. Ber. Dtsch. Chem. Ges. B192154220420910.1002/cber.19210540206
    [Google Scholar]
  26. (a WibautJ.P. OverhoffJ. Recl. Trav. Chim. Pays Bas19284776176310.1002/recl.19280470906
    [Google Scholar]
  27. (b den HertogH.J. WibautJ.P. Recl. Trav. Chim. Pays Bas193655212213010.1002/recl.19360550204
    [Google Scholar]
  28. HeinF. RetterW. Ber. Dtsch. Chem. Ges. B19286181790179110.1002/cber.19280610837
    [Google Scholar]
  29. NelsonT.D. CrouchR.D. Org. React.200463265555
    [Google Scholar]
  30. HenningsD.D. IwamaT. RawalV.H. Org. Lett.1999181205120810.1021/ol990872+
    [Google Scholar]
  31. (a PenalvaV. HassanJ. LavenotL. GozziC. LemaireM. Tetrahedron Lett.199839172559256010.1016/S0040‑4039(98)00196‑8
    [Google Scholar]
  32. (b HassanJ. PenalvaV. LavenotL. GozziC. LemaireM. Tetrahedron19985445137931380410.1016/S0040‑4020(98)00849‑7
    [Google Scholar]
  33. LakshmideviJ. AppaR.M. NaiduB.R. PrasadS.S. SarmaL.S. VenkateswarluK. Chem. Commun. (Camb.)20185487123331233610.1039/C8CC06940A30320316
    [Google Scholar]
  34. WebbD.A. AlsudaniZ. XuG. GaoP. ArnoldL.A. RSC Sustainability2023161522152910.1039/D3SU00005B38013944
    [Google Scholar]
  35. LeeK. LeeP.H. Tetrahedron Lett.200849274302430510.1016/j.tetlet.2008.04.123
    [Google Scholar]
  36. LiC. ShiY. ChenQ. ZhangK. YangG. J. Org. Chem.20238842306231310.1021/acs.joc.2c0271736719812
    [Google Scholar]
  37. YllmazÜ. DenizS. KüçükbayH. ȘireciN. Molecules2013183712372410.3390/molecules1804371223529031
    [Google Scholar]
  38. HuangY. LiuL. FengW. ChemistrySelect20161363063410.1002/slct.201600181
    [Google Scholar]
  39. Nicasio-CollazoJ. WrobelK. WrobelK. SerranoO. New J. Chem.201741178729873310.1039/C7NJ02468A
    [Google Scholar]
  40. ManosoA.S. DeShongP. J. Org. Chem.200166227449745510.1021/jo010621q11681960
    [Google Scholar]
  41. KuroboshiM. WakiY. TanakaH. J. Org. Chem.200368103938394210.1021/jo020747312737575
    [Google Scholar]
  42. ZengM. DuY. ShaoL. QiC. ZhangX.M. J. Org. Chem.20107582556256310.1021/jo100089d20302294
    [Google Scholar]
  43. HajipourA.R. RafieeF. Appl. Organomet. Chem.201529314715110.1002/aoc.3260
    [Google Scholar]
  44. WatersG.D. CarrickJ.D. RSC Advances20201018108071081510.1039/D0RA00673D35492897
    [Google Scholar]
  45. TianX. GuoY. AnW. RenY.L. QinY. NiuC. ZhengX. Nat. Commun.2022131618610.1038/s41467‑022‑33778‑936261445
    [Google Scholar]
  46. PuthiyarajP. AhnW-S. Mol. Catal.2017437737910.1016/j.mcat.2017.05.003
    [Google Scholar]
  47. DubeyA.V. KumarA.V. Appl. Organomet. Chem.2020345e557010.1002/aoc.5570
    [Google Scholar]
  48. SenguptaD. PandeyM.K. MondalD. RadhakrishnaL. BalakrishnaM.S. Eur. J. Inorg. Chem.20182018293374338310.1002/ejic.201800291
    [Google Scholar]
  49. RasouliM.A. RanjbarP.R. Z. Naturforsch. B. J. Chem. Sci.201368894695010.5560/znb.2013‑3048
    [Google Scholar]
  50. MoghaddamF.M. PourkavehR. KarimiA. AyatiS.E. Asian J. Org. Chem.20187480280910.1002/ajoc.201800041
    [Google Scholar]
  51. BhowmikT. SadhukhanM. KempasiddaiahM. BarmanS. Appl. Organomet. Chem.2022364e661310.1002/aoc.6613
    [Google Scholar]
  52. SutarD.J. ZendeS.N. MhaldarP.M. PoreD.M. TapaseA.S. GokaviG.S. Catal. Lett.202415431209121810.1007/s10562‑023‑04378‑z
    [Google Scholar]
  53. DhitalR.N. KamonsatikulC. SomsookE. SakuraiH. Catal. Sci. Technol.20133113030303510.1039/c3cy00303e
    [Google Scholar]
  54. TyagiA. YamamotoA. YoshidaH. Catal. Sci. Technol.20188236196620310.1039/C8CY01866A
    [Google Scholar]
  55. ChenG. DuF. ZhouQ. LiuD. FangT. ShiY. DuY. Synlett201829677978410.1055/s‑0036‑1591892
    [Google Scholar]
  56. TieccoM. TestaferriL. TingoliM. ChianelliD. MontanucciM. Synthesis19841984973673810.1055/s‑1984‑30951
    [Google Scholar]
  57. (a NaumannC. LanghalsH. Synthesis19901990427928110.1055/s‑1990‑26852
    [Google Scholar]
  58. (b TrécourtF. MalletM. MonginO. GervaisB. QuéguinerG. Tetrahedron199349378373838010.1016/S0040‑4020(01)81920‑7
    [Google Scholar]
  59. FortY. BeckerS. CaubèreP. Tetrahedron19945041118931190210.1016/S0040‑4020(01)89303‑0
    [Google Scholar]
  60. LinG. HongR. J. Org. Chem.200166217234723410.1021/jo012948x
    [Google Scholar]
  61. IyodaM. OtsukaH. SatoK. NisatoN. OdaM. Bull. Chem. Soc. Jpn.1990631808710.1246/bcsj.63.80
    [Google Scholar]
  62. ZhangB. BreslowR. J. Am. Chem. Soc.199711971676168110.1021/ja963769d
    [Google Scholar]
  63. StangeA.F. TokuraS. KiraM. J. Organomet. Chem.20006121-211712410.1016/S0022‑328X(00)00429‑0
    [Google Scholar]
  64. RajalakshmananE. AlexanderV. Synth. Commun.200535689189510.1081/SCC‑200051056
    [Google Scholar]
  65. WeixD. BuonomoJ. EversonD. Synthesis201345223099310210.1055/s‑0033‑133852025221358
    [Google Scholar]
  66. XüM. WuS. ZouG. Eur. J. Org. Chem.20242739e20240062510.1002/ejoc.202400625
    [Google Scholar]
  67. LiaoL.Y. KongX.R. DuanX.F. J. Org. Chem.201479277778210.1021/jo402084m24367890
    [Google Scholar]
  68. CassolT.M. DemnitzF.W.J. NavarroM. NevesE.A. Tetrahedron Lett.200041438203820610.1016/S0040‑4039(00)01310‑1
    [Google Scholar]
  69. de FrançaK.W.R. NavarroM. LéonelÉ. DurandettiM. NédélecJ.Y. J. Org. Chem.20026761838184210.1021/jo016280y11895400
    [Google Scholar]
  70. OliveiraJ.L. SilvaM.J. FlorêncioT. UrginK. SengmanyS. LéonelE. NédélecJ.Y. NavarroM. Tetrahedron201268102383239010.1016/j.tet.2012.01.017
    [Google Scholar]
  71. ToumminiD. OuazzaniF. TailleferM. Org. Lett.201315184690469310.1021/ol401987s24004324
    [Google Scholar]
  72. LiuY. BergèsJ. ZaidY. ChahdiF.O. Van Der LeeA. HarakatD. ClotE. JaroschikF. TailleferM. J. Org. Chem.20198474413442010.1021/acs.joc.8b0283430665303
    [Google Scholar]
  73. PalA. ThakurA. Org. Biomol. Chem.202220458977898710.1039/D2OB01738E36326160
    [Google Scholar]
  74. BadgerG.M. SasseW.H.F. J. Chem. Soc.195661662010.1039/jr9560000616
    [Google Scholar]
  75. AcharS. ScottJ.D. VittalJ.J. PuddephattR.J. Organometallics199312114592459810.1021/om00035a051
    [Google Scholar]
  76. BaoJ. ZhouY. ZhangY. WangY. LiangS. GuoZ. GuoC. XueY. ZhuangT. HuY. J. Catal.20203909010210.1016/j.jcat.2020.07.032
    [Google Scholar]
  77. RosevearP.E. SasseW.H.F. J. Heterocycl. Chem.19718348348510.1002/jhet.5570080322
    [Google Scholar]
  78. HaddaT.B. BozecH.L. Inorg. Chim. Acta199320410310710.1016/S0020‑1693(00)88119‑0
    [Google Scholar]
  79. RoboM.T. PrinsellM.R. WeixD.J. J. Org. Chem.20147921106241062810.1021/jo501925s25343728
    [Google Scholar]
  80. KawashimaT. TakaoT. SuzukiH. J. Am. Chem. Soc.200712936110061100710.1021/ja074224u17705495
    [Google Scholar]
  81. TakaoT. KawashimaT. KandaH. OkamuraR. SuzukiH. Organometallics201231134817483110.1021/om300379d
    [Google Scholar]
  82. NagaokaM. KawashimaT. SuzukiH. TakaoT. Organometallics201635142348236010.1021/acs.organomet.6b00277
    [Google Scholar]
  83. YamadaS. KanedaT. SteibP. MurakamiK. ItamiK. Angew. Chem. Int. Ed.201958258341834510.1002/anie.201814701
    [Google Scholar]
  84. YangY. LanJ. YouJ. Chem. Rev.2017117138787886310.1021/acs.chemrev.6b0056728085272
    [Google Scholar]
  85. (a ShangR. IliesL. NakamuraE. Chem. Rev.2017117139086913910.1021/acs.chemrev.6b0077228378590
    [Google Scholar]
  86. (b GandeepanP. MüllerT. ZellD. CeraG. WarratzS. AckermannL. Chem. Rev.201911942192245210.1021/acs.chemrev.8b0050730480438
    [Google Scholar]
  87. (c WhitehurstW.G. KimJ. KoenigS.G. ChirikP.J. J. Am. Chem. Soc.202214441191861919510.1021/jacs.2c0886536194198
    [Google Scholar]
  88. DavinL. CleggW. KennedyA.R. ProbertM.R. McLellanR. HeviaE. Chemistry20182455148301483510.1002/chem.20180329730051933
    [Google Scholar]
  89. (a MaoJ. WangY-B. YangL. XiangS. WuQ. CuiY. QianL. Nat. Chem.20211398299110.1038/s41557‑021‑00750‑x34373595
    [Google Scholar]
  90. (b MurtazaA. UlhaqZ. ShirinfarB. RaniS. AslamS. MartinsG.M. AhmedN. Chem. Rec.20232310e20230011910.1002/tcr.202300119
    [Google Scholar]
  91. (c BanikA. PairaR. ShawB.K. VijaykumarG. MandalS.K. J. Org. Chem.20188363236324410.1021/acs.joc.8b0014029436824
    [Google Scholar]
/content/journals/loc/10.2174/0115701786350613250118104808
Loading
/content/journals/loc/10.2174/0115701786350613250118104808
Loading

Data & Media loading...

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