Skip to content
2000
Volume 13, Issue 2
  • ISSN: 2211-5447
  • E-ISSN: 2211-5455

Abstract

Introduction

The gold-catalyzed benzannulation reaction of oxo-alkynes with alkenes or alkynes is one of the important and unique reactions in gold-catalyzed organic transformations.

Methods

In this manuscript, many facets of this reaction have been discussed concerning reactivity and selectivity, along with a new self-benzannulation process. The scope of this chemistry was extended to construct a phenanthrene moiety.

Results

In addition, a palladium-gold dual catalytic arylation of isobenzopyrylium salts using arene-diazonium salts as an aryl group source and a one-pot isoquinoline synthesis is reported for the first time.

Conclusion

Moreover, a conductance measurement experiment was performed, which supports the formation of ionic species, most likely the isobenzopyrylium auric ate complex as an intermediate formed during the reaction process.

Loading

Article metrics loading...

/content/journals/ccat/10.2174/0122115447296524240815114327
2024-08-26
2025-04-16
Loading full text...

Full text loading...

References

  1. YuJ. WangX. XuM. ZhangB. XiongZ. MaoH. LvX. ZhouL. Synthesis of α-pyrones via gold-catalyzed cycloisomerization/[2 + 1] cycloaddition/rearrangement of enyne-amides and sulfur ylides.Org. Chem. Front.202310491692210.1039/D2QO01388F
    [Google Scholar]
  2. KumarA. DasA. PatilN.T. Gold-catalyzed aryl-alkenylation of alkenes.Org. Lett.202325162934293810.1021/acs.orglett.3c01044 37058129
    [Google Scholar]
  3. MackenrothA.V. AntoniP.W. RomingerF. RudolphM. HashmiA.S.K. Gold-catalyzed [3,3]-sigmatropic rearrangement of ortho -Alkynyl- S, S -diarylsulfilimines.Org. Lett.202325162907291210.1021/acs.orglett.3c00953 37071638
    [Google Scholar]
  4. SanilG. KrzeszewskiM. ChaładajW. DanikiewiczW. KnyshI. DobrzyckiŁ. Staszewska-KrajewskaO. CyrańskiM.K. JacqueminD. GrykoD.T. Gold‐catalyzed 1,2‐aryl shift and double alkyne benzannulation.Angew. Chem. Int. Ed.20236249e20231112310.1002/anie.202311123 37823245
    [Google Scholar]
  5. StylianakisI. KolocourisA. Comprehensive overview of homogeneous gold-catalyzed transformations of π-systems for application scientists.Catalysts202313692110.3390/catal13060921
    [Google Scholar]
  6. KoleyM. HanJ. SoloshonokV.A. MojumderS. JavahershenasR. MakaremA. External oxidants in gold-catalyzed cross-coupling reactions.J. Coord. Chem.2024771-214810.1080/00958972.2023.2286182
    [Google Scholar]
  7. GhoshT. BhaktaS. Advancements in gold‐catalyzed cascade reactions to access carbocycles and heterocycles: An overview.Chem. Rec.2023233e20220022510.1002/tcr.202200225 36543388
    [Google Scholar]
  8. PraveenC. SzafertS. Homogeneous gold catalysis for regioselective carbocyclization of alkynyl precursors.ChemPlusChem2023887e20230020210.1002/cplu.202300202 37285057
    [Google Scholar]
  9. AmbegaveS.B. Shubham MoreT.R. PatilN.T. Gold-based enantioselective bimetallic catalysis.Chem. Commun.202359528007801610.1039/D3CC01966G 37285287
    [Google Scholar]
  10. PatilN.T. AmbegaveS.B. Gold-catalyzed cross-coupling and 1,2-difunctionalization reactions: A personal account.Synlett202334769870810.1055/a‑1893‑7653
    [Google Scholar]
  11. ArcadiA. GiuseppeS. Recent applications of gold catalysis in organic synthesis.Curr. Org. Chem.20048979581210.2174/1385272043370564
    [Google Scholar]
  12. WeiC. LiC.J. Gold-catalyzed coupling of alkynes and acyl iminiums.Lett. Org. Chem.20052541041410.2174/1570178054405959
    [Google Scholar]
  13. NguyenT. Seon-MenielB. JullianJ.C. FigadereB. Gold-catalyzed regioselective hydration of homopropargyl alcohols followed by diastereoselective reduction: an easy access to cis 2,5-disubstituted tetrahydrofurans.Lett. Org. Chem.20096863063610.2174/157017809790442989
    [Google Scholar]
  14. PandaB. Emerging technologies for sustainable development (icetsd-19)”, gold catalyzed benzannulation of pyridine-containing oxoalkynes: Mechanistic investigations.Boca RatonCRC Press20196872
    [Google Scholar]
  15. PandaB. Gold catalysts with highly electronegative counter ions: an investigative overview.Communique2019121
    [Google Scholar]
  16. KumarP.B. DamodarK. SuneelK. Gold-catalyzed reactions of substituted 1,5-diynes: recent advances and their chemistry.Mini Rev. Org. Chem.202421442443510.2174/1570193X20666230302114722
    [Google Scholar]
  17. KaurN. Gold catalysts in the synthesis of five-membered n-heterocycles.Curr. Organocatal.20174212215410.2174/2213337204666171103142349
    [Google Scholar]
  18. MartíÀ. OgallaG. EchavarrenA.M. Hydrogen-bonded matched ion pair gold(i) catalysis.ACS Catal.20231315102171022310.1021/acscatal.3c02638 37560194
    [Google Scholar]
  19. FangQ.Y. HanJ. QinM. LiW. ZhuC. XieJ. Trinuclear gold‐catalyzed 1,2‐difunctionalization of alkenes.Angew. Chem. Int. Ed.20236234e20230512110.1002/anie.202305121 37170888
    [Google Scholar]
  20. AmbegaveS.B. SGold-based enantioselective bimetallic catalysis.Chem. Commun.2023598007801610.1039/D3CC01966G 37285287
    [Google Scholar]
  21. WangW. DingM. ZhaoC.G. ChenS. ZhuC. HanJ. LiW. XieJ. Unlocking migratory insertion in gold redox catalysis.Angew. Chem. Int. Ed.20236229e20230401910.1002/anie.202304019 37188636
    [Google Scholar]
  22. LiuD.Y. HanJ. LiuK. ChengY. TanH. YangX. LiW. XieJ. Dinuclear gold‐catalyzed para ‐selective c−h arylation of undirected arenes by noncovalent interactions.Angew. Chem. Int. Ed.20236244e20231312210.1002/anie.202313122 37707123
    [Google Scholar]
  23. BhoyareV.W. TatheA.G. GandonV. PatilN.T. Unlocking the chain‐walking process in gold catalysis**.Angew. Chem. Int. Ed.20236246e20231278610.1002/anie.202312786
    [Google Scholar]
  24. BhoyareV.W. Sosa CarrizoE.D. ChintawarC.C. GandonV. PatilN.T. Gold-catalyzed heck reaction.J. Am. Chem. Soc.2023145168810881610.1021/jacs.3c02544 37061943
    [Google Scholar]
  25. TeixeiraP. BastinS. CésarV. Fused polycyclic nhc ligands in gold catalysis: Recent advances.Isr. J. Chem.2023639e20220005110.1002/ijch.202200051
    [Google Scholar]
  26. DasA. PatilN.T. Ligand-enabled gold-catalyzed c(sp2)–o cross-coupling reactions.ACS Catal.20231363847385310.1021/acscatal.3c00338
    [Google Scholar]
  27. TatheA.G. SaswadeS.S. PatilN.T. Gold-catalyzed multicomponent reactions.Org. Chem. Front.20231092359238410.1039/D3QO00272A
    [Google Scholar]
  28. León RojasA.F. KyneS.H. ChanP.W. Recent advances in the gold-catalyzed reactions of propargyl esters.Acc. Chem. Res.202356121406142010.1021/acs.accounts.3c00057 37278450
    [Google Scholar]
  29. PandaB. Use of gold nanoparticles in the synthesis of heterocyclic compounds.Lett. Org. Chem.2023201182710.2174/1570178619666220826115245
    [Google Scholar]
  30. PandaB. SarkarT.K. Gold catalysis: regio- and stereoselective total synthesis of xyloketals D and G and the related natural product alboatrin.J. Org. Chem.20137862413242110.1021/jo302545n 23428314
    [Google Scholar]
  31. PandaB. Total synthesis of xyloketals and related natural product alboatrin: strategies and tactics.ChemistrySelect20194319143916410.1002/slct.201900779
    [Google Scholar]
  32. PandaB. Total synthesis of bruguierols: Strategies and tactics.Arkivoc20192019129330310.24820/ark.5550190.p010.966
    [Google Scholar]
  33. PandaB. GooyeeA.K. Bioactivity of marine natural product xyloketals.Lett. Org. Chem.202118750751210.2174/1570178617999200909114431
    [Google Scholar]
  34. PflästererD. HashmiA.S. Gold catalysis in total synthesis – recent achievements.Chem. Soc. Rev.20164551331136710.1039/C5CS00721F 26673389
    [Google Scholar]
  35. DeS. DanA.K. SahuR. ParidaS. DasD. Total synthesis of natural products using gold catalysis.Chem. Asian J.20221724e20220089610.1002/asia.202200896 36256453
    [Google Scholar]
  36. PandaB. SarkarT.K. Gold and palladium combined for the Sonogashira-type cross-coupling of arenediazonium salts.Chem. Commun.201046183131313310.1039/c001277g 20361097
    [Google Scholar]
  37. PandaB. Sonogashira coupling of arenediazonium salts: discovery and developments.Arkivoc20212021917719910.24820/ark.5550190.p011.559
    [Google Scholar]
  38. PandaB. SarkarT.K. On the catalytic duo PdCl2(PPh3)2/AuCl(PPh3) that cannot effect a Sonogashira-type reaction: a correction.Tetrahedron Lett.201051230130510.1016/j.tetlet.2009.11.003
    [Google Scholar]
  39. PandaB. SarkarT.K. Gold and palladium combined for the sonogashira coupling of aryl and heteroaryl halides Synthesis20134508170829
    [Google Scholar]
  40. PandaB. Joy and challenges of alkynylation of arenes and heteroarenes through double c−h functionalizations.Asian J. Org. Chem.20209449250710.1002/ajoc.201900733
    [Google Scholar]
  41. PandaB. Progress in catalytic decarboxylative oxidative c-h alkynylation.Curr. Catal.202211121510.2174/2211544711666220210125547
    [Google Scholar]
  42. PandaB. Organocatalytic c-h bond functionalizations for the synthesis of heterocyclesCurr. Organocatal.202310.2174/2213337210666230213120833
    [Google Scholar]
  43. PandaB. Microwave-assisted homogeneous gold catalyzed organic transformations.Curr. Microw. Chem.20207316618210.2174/2213335607999200811130113
    [Google Scholar]
  44. ChemistryO. Homogeneous gold catalysis under microwave irradiation: a greener approach.Organomet. Chem2022446891
    [Google Scholar]
  45. HeY. ZhengZ. LiuQ. ZhangX. FanX. Solvent-regulated coupling of 2-alkynylbenzaldehydes with cyclic amines: selective synthesis of fused n-heterocycles and functionalized naphthalene derivatives.Org. Lett.202022229053905810.1021/acs.orglett.0c03442 33151081
    [Google Scholar]
  46. CaiL. ChenY. CaoH. WeiQ. YangY. OuyangQ. PengY. Asymmetric cyclization/nucleophilic tandem reaction of o -alkynylacetophenone with (diazomethyl)phosphonate for the synthesis of functional isochromenes.Org. Lett.201921187597760110.1021/acs.orglett.9b02864 31478383
    [Google Scholar]
  47. ChenJ. HuR. BaoQ. ShangD. YuL. ChanP.W.H. RaoW. Ligand-controlled chemoselectivity in gold-catalyzed cascade cyclization of 1,4-diene-tethered 2-alkynylbenzaldehydes.Org. Chem. Front.20229236520652910.1039/D2QO01346K
    [Google Scholar]
  48. YangW.L. ShangX.Y. NiT. YanH. LuoX. ZhengH. LiZ. DengW.P. Diastereo‐ and enantioselective synthesis of bisbenzannulated spiroketals and spiroaminals by ir/ag/acid ternary catalysis.Angew. Chem. Int. Ed.20226142e20221020710.1002/anie.202210207 35924328
    [Google Scholar]
  49. YuY. WangX.Y. PengJ.Y. LiuT. ZhaoY.L. Copper-catalyzed cascade cyclization reaction of 3-aminocyclobutenones with electron-deficient internal alkynes: synthesis of fully substituted indoles.Chem. Commun.202056689815981810.1039/D0CC00512F 32706346
    [Google Scholar]
  50. WangD. WangS.C. HaoW.J. TuS.J. JiangB. Selective syntheses of benzo[ b]carbazoles and c3‐substituted indoles via tunable catalytic annulations of β ‐alkynyl ketones with indoles.Adv. Synth. Catal.2020362163416342210.1002/adsc.202000491
    [Google Scholar]
  51. AsaoN. TakahashiK. LeeS. KasaharaT. YamamotoY. AuCl3-catalyzed benzannulation: synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes.J. Am. Chem. Soc.200212443126501265110.1021/ja028128z 12392398
    [Google Scholar]
  52. AsaoN. AikawaH. YamamotoY. AuBr(3)-catalyzed [4 + 2] benzannulation between an enynal unit and enol.J. Am. Chem. Soc.2004126247458745910.1021/ja0477367 15198590
    [Google Scholar]
  53. DykerG. HildebrandtD. LiuJ. MerzK. Gold(III) chloride catalyzed domino processes with isobenzopyrylium cation intermediates.Angew. Chem. Int. Ed.200342364399440210.1002/anie.200352160 14502722
    [Google Scholar]
  54. DykerG. HildebrandtD. Total synthesis of heliophenanthrone.J. Org. Chem.200570156093609610.1021/jo050400a 16018708
    [Google Scholar]
  55. AsaoN. AikawaH. Lewis acid-catalyzed [4 + 2] benzannulation between enynal units and enols or enol ethers: novel synthetic tools for polysubstituted aromatic compounds including indole and benzofuran derivatives.J. Org. Chem.200671145249525310.1021/jo060597m 16808512
    [Google Scholar]
  56. AsaoN. SatoK. Aucl-catalyzed [4+2] benzannulation between o -alkynyl(oxo)benzene and benzyne.Org. Lett.20068235361536310.1021/ol062268m 17078718
    [Google Scholar]
  57. SatoK. AsaoN. YamamotoY. Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4 + 2] benzannulation: enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2.J. Org. Chem.200570228977898110.1021/jo051444m 16238336
    [Google Scholar]
  58. PandaB. BhadraJ. SarkarT.K. An approach to highly functionalized quinolines and isoquinolines via a gold-catalyzed benzannulation.Synlett2011689693
    [Google Scholar]
  59. KimN. KimY. ParkW. SungD. GuptaA.K. OhC.H. Gold-catalyzed cycloisomerization of o-alkynylbenzaldehydes with a pendant unsaturated bond: [3 + 2] cycloaddition of gold-bound 1,3-dipolar species with dipolarophiles.Org. Lett.20057235289529110.1021/ol052229v 16268560
    [Google Scholar]
  60. PandaB. Thorpe-Ingold effect assisted Strained Ring Synthesis.MalaysiaLincoln University of College202210.31674/book.2022macbs.005
    [Google Scholar]
  61. SarkarT. PandaB. Gold-catalyzed benzannulation of electronically rich/rich and deficient/deficient oxoalkynes with alkynes.Synthesis20134591227123410.1055/s‑0032‑1318454
    [Google Scholar]
  62. AsaoN. Gold- and copper-catalyzed [4+2] benzannulations between enynal or enynone units and 2π-systems.Synlett20062006111645165610.1055/s‑2006‑947331
    [Google Scholar]
  63. UmedaR. UedaR. TanakaT. HayashiA. IkeshitaM. SuzukiS. NaotaT. NishiyamaY. Selective synthesis of 1-halonaphthalenes by copper-catalyzed benzannulation.Tetrahedron20217913187210.1016/j.tet.2020.131872
    [Google Scholar]
  64. GiriS.S. LiuR-S. Copper-catalyzed [4+2]-cycloadditions of isoxazoles with 2-alkynylbenzaldehydes to access distinct α-carbonylnaphthalene derivatives: c(3,4)- versus c(4,5)-regioselectivity at isoxazoles.ACS Catal.2019987328733410.1021/acscatal.9b02323
    [Google Scholar]
  65. PandaB. Catalytic alkynylations through the activation of C-N bonds.Arkivoc20232023210.24820/ark.5550190.p012.011
    [Google Scholar]
  66. PandaB. AlbanoG. DMF as co surrogate in carbonylation reactions: principles and application to the synthesis of heterocycles.Catalysts20211112153110.3390/catal11121531
    [Google Scholar]
  67. MalhotraD. LiuL.P. MashutaM.S. HammondG.B. Gold-catalyzed annulations of 2-alkynyl benzaldehydes with vinyl ethers: synthesis of dihydronaphthalene, isochromene, and bicyclo[2.2.2]octane derivatives.Chem. Eur. J201319124043405010.1002/chem.201203841 23362089
    [Google Scholar]
  68. GilchristT.L. HealyM.A. Preparation of 1-substituted-3,4-dihydronaphthalene-2-carboxaldehyde N,N-dimethylhydrazones by palladium(0) coupling, and their electrocyclic ring closure.Tetrahedron199349122543255610.1016/S0040‑4020(01)86333‑X
    [Google Scholar]
  69. PandaB. BasakS. HazraA. SarkarT.K. A domino Michael-Dieckmann-Peterson approach to the synthesis of substituted hydroxyquinolines and hydroxyisoquinolines.J. Chem. Res.201034210911310.3184/030823410X12659067482702
    [Google Scholar]
  70. PandaB. Synthetic studies directed towards (-)-chrysanthone a: facile synthesis of a tricyclic lactone intermediate.J. Indian Chem. Soc.201996231239
    [Google Scholar]
  71. PandaB. Gold Catalysis and in Synergy with Palladium2018
    [Google Scholar]
  72. PandaJ. MohapatraS. Ansar AhemadM. NayakS. MohapatraS. Transition‐metal catalyzed [4+2]‐cycloaddition reactions: A sexennial update.ChemistrySelect2024912e20230364310.1002/slct.202303643
    [Google Scholar]
  73. BaoQ. ChenJ. LiuZ. RaoW. Direct construction of biaryl-bridged 8–11 membered N -heterocycles via gold(I)-catalyzed intramolecular [4 + 2] benzannulation of N -tethered diynyl benzaldehydes.Org. Chem. Front.202310133280328710.1039/D3QO00250K
    [Google Scholar]
  74. ShangD. HuR. BaoQ. ChenJ. YuL. ChanP.W. RaoW. PtI 4 -catalyzed oxidative and hydrogenative dearomative [3 + 2] cycloaddition of 1 H -indole N -tethered o -alkynylbenzaldehydes.Org. Chem. Front.202210114014910.1039/D2QO01520J
    [Google Scholar]
  75. ZhongJ. HuR. SangJ. RaoW. Gold(I)-catalyzed intramolecular [4 + 2] cycloaddition of ortho-(N-tethered 1,6-diynyl)benzaldehydes to 3,4-dihydrobenzo[f]isoquinolin-1(2H)-ones.Tetrahedron Lett.2020613115220010.1016/j.tetlet.2020.152200
    [Google Scholar]
  76. LiuY. IzzoJ.A. McLeodD. RičkoS. SvenningsenE.B. PoulsenT.B. JørgensenK.A. Organocatalytic asymmetric multicomponent cascade reaction for the synthesis of contiguously substituted tetrahydronaphthols.J. Am. Chem. Soc.2021143218208822010.1021/jacs.1c03923 34028261
    [Google Scholar]
  77. LiX.S. HanY.P. XuD. LiM. WeiW.X. LiangY.M. Silver trifluoromethanesulfonate-catalyzed annulation of propargylic alcohols with 3-methyleneisoindolin-1-one.J. Org. Chem.20208542626263410.1021/acs.joc.9b02533 31880453
    [Google Scholar]
  78. HuD. PiC. HuW. HanX. WuY. CuiX. Ru(III)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources.Chin. Chem. Lett.20223384064406810.1016/j.cclet.2021.12.072
    [Google Scholar]
  79. LiuS. QianH. ZhangT. XieH. HanZ. GuoW. HuangH. SunJ. Mild intermolecular synthesis of a cyclopropane‐containing tricyclic skeleton: unusual reactivity of isobenzopyryliums.Angew. Chem. Int. Ed.20216039212722127610.1002/anie.202108258 34342934
    [Google Scholar]
  80. Sekar Kulandai RajA. LiuR.S. Gold‐catalyzed [4+3]‐annulations of benzopyriliums with vinyldiazo carbonyls to form bicyclic heptatriene rings with skeletal rearrangement.Adv. Synth. Catal.2020362122517252210.1002/adsc.202000292
    [Google Scholar]
/content/journals/ccat/10.2174/0122115447296524240815114327
Loading
/content/journals/ccat/10.2174/0122115447296524240815114327
Loading

Data & Media loading...

Supplements

Supplementary material is available on the publishers' website along with the published article.


  • Article Type:
    Research Article
Keyword(s): benzannulation; catalysis; Gold; Isobenzopyrylium salts; isoquinolines; quinolines
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