Lewis Acid-catalyzed Regioselective Addition of Allenoates to Indoles for Synthesis of Bisindolylesters

Abstract

Indole derivatives, especially bisindolylesters, have attracted intense attention due to their important applications in medicinal chemistry and organic synthesis. Here we develop a Lewis acid-catalyzed efficient and regioselective strategy to prepare a series of symmetric and unsymmetric bisindolylesters in high to excellent yields under mild conditions. The systematic investigations, which include stoichiometric nuclear magnetic resonance (NMR) experiments and structural characterization of intermediates, have provided insights into the possible reaction mechanism for this B(C₆F₅)₃-catalyzed addition reaction. Moreover, the sequential employment of Al(C₆F₅)₃ and B(C₆F₅)₃ as catalysts enabled us to successfully prepare the unsymmetric bisindolyl-compounds in one-pot two-step manner without the separation step.

Keywords

B(C₆F₅)₃ / Al(C₆F₅)₃ / Indole / Allenoate / Indolylester

References

[1] HowardM F, BinaX R, BinaJ Infect. Immun., 2019, 87: e00776-18

[2] KaramyanA J K, HamannM T Chem. Rev., 2010, 110: 4489

[3] WenJ, ShiZ Acc. Chem. Res., 2021, 54: 1723

[4] BandiniM, EichholzerA Angew. Chem. Int. Ed., 2009, 48: 9608

[5] LeeJ Nutr. Cancer., 2019, 71: 992

[6] IchiteN, ChouguleM B, JacksonT, FulzeleS V, SafeS, SinghM Clin. Cancer Res., 2009, 15: 543

[7] ZongJ, WuQ Q, ZhouH, ZhangJ Y, YuanY, BianZ Y, DengW, DaiJ, LiF F, XuM, FangY, TangQ Z Mol. Med. Rep., 2015, 12: 1247

[8] PrioreD G, GudipudiD K, MontemaranoN, RestivoA M, StegaJ M, ArslanA A Gynecol. Oncol., 2010, 116: 464

[9] KangJ, GaoY, ZhangM, DingX, WangZ, MaD, WangQ J. Agric. Food Chem., 2020, 68: 7839

[10] RoyS, GajbhiyeR, MandalM, PalC, MeyyapanA, MukherjeeJ, JaisankarP Med. Chem. Res., 2014, 23: 1371

[11] OsawaT, NamikiM, SuzukiK, MitsuokaT Mutat. Res., 1983, 122: 299

[12] BartoliG, BoscoM, FogliaG, GiulianiA, MarcantoniE, SambriL Synthesis, 2004, 6: 0895

[13] YangT, LuH, ShuY, OuY, HongL, AuC T, QiuR Org. Lett., 2020, 22: 827

[14] LeeS O, ChoiJ, KookS, LeeS Y Org. Biomol. Chem., 2020, 18: 9060

[15] SimhaP R, MangaliM S, GariD K, VenkatapuramP, AdivireddyP J. Heterocyclic Chem., 2017, 54: 2717

[16] BudaniaS, ShelkeG M, KumarA Synth. Commun., 2017, 47: 646

[17] KothandapaniJ, GanesanA, ManiG K, KulandaisamyA J, RayappanJ B B, GanesanS S Tetrahedron Lett., 2016, 57: 3472

[18] VeisiH, MalekiB, EshbalaF H, VeisiH, MastiR, AshrafiS S, BaghayeriM RSC Adv., 2014, 4: 30683

[19] HouC, SunC, WangC, JiaX, ChangW ACS Sustainable Chem. Eng., 2013, 1: 549

[20] ReddyB V S, RajeswariN, SarangapaniM, PrashanthiY, GanjiR J, AddlagattaA Bioorg. Med. Chem. Lett., 2012, 22: 2460

[21] TayebeeR, NehzatF, SereshtE R, MohammadiF Z, RafieeE J. Mol. Catal. A: Chem., 2011, 351: 154

[22] AzizianJ, MohammadiA A, KarimiN, MohammadizadehM R, KarimiA R Catal. Commun., 2006, 7: 752

[23] JatK P, DabariaK K, BaiR, YadavL, BadsaraS S J. Org. Chem., 2022, 87: 12975

[24] ZhaoY S, RuanH L, WangX Y, ChenC, SongP F, LüC W, ZouL W RSC Adv., 2019, 9: 40168

[25] LafziF, KilicH, SaracogluN J. Org. Chem., 2019, 84: 12120

[26] ChintaB S, BaireB Tetrahedron, 2016, 72: 8106

[27] SwethaA, BabuB M, MeshramH M Tetrahedron Lett., 2015, 56: 1775

[28] ChakrabortiA K, RoyS R, KumarD, ChopraP Green Chem., 2008, 10: 1111

[29] NairV, AbhilashK G, VidyaN Org. Lett., 2005, 7: 5857

[30] JiS J, WangS Y, ZhangY, LohT P Tetrahedron, 2004, 60: 2051

[31] NagarajanR, PerumalP T Tetrahedron, 2002, 58: 1229

[32] SantosA S, FerroR D, ViduedoN, MaiaL B, SilvaA M S, MarquesM M B ChemistryOpen, 2023, 12: e202200265

[33] BiswasN, SharmaR, SrimaniD Adv. Synth. Catal., 2020, 362: 2902

[34] ArunV, RoyL, SarkarS D Chem. Eur. J., 2020, 26: 16649

[35] SunC, ZouX, LiF Chem. Eur. J., 2013, 19: 14030

[36] TyagiA, KhanJ, YadavN, MahatoR, HazraC K J. Org. Chem., 2022, 87: 10229

[37] MoreA A, SzpilmanA M Org. Lett., 2020, 22: 3759

[38] YuanZ, ChenS, WengZ Org. Chem. Front., 2020, 7: 482

[39] LeiL S, WangB W, JinD P, GaoZ P, LiangH, WangS H, XuX T, ZhangK, ZhangX Y Adv. Synth. Catal., 2020, 362: 2870

[40] ChengL T, LuoS Q, HongB C, ChenC L, LiW S, LeeG H Org. Biomol. Chem., 2020, 18: 6247

[41] AbeT, NakamuraS, YanadaR, ChoshiT, HibinoS, IshikuraM Org. Lett., 2013, 15: 3622

[42] AlonsoI, EsquiviasJ, ArrayásR G, CarreteroJ C J. Org. Chem., 2008, 73: 6401

[43] RuepingM, NachtsheimB J, MorethS A, BolteM Angew. Chem. Int. Ed., 2008, 47: 593

[44] KumarS, KumarV, ChimniS S Tetrahedron Lett., 2003, 44: 2101

[45] JadhavS D, BakshiD, SinghA J. Org. Chem., 2015, 80: 10187

[46] JeonJ, RyuH, LeeC, ChoD, BaikM H, HongS J. Am. Chem. Soc., 2019, 141: 10048

[47] YoungP C, HadfieldM S, ArrowsmithL, MacleodK M, MuddR J, HoreJ A J, LeeA L Org. Lett., 2012, 14: 898

[48] McLeanE B, CutoloF M, CassidyO J, BurnsD J, LeeA L Org. Lett., 2020, 22: 6977

[49] LiuT W, ZhangS T, HeJ H, ZhangY T Chem. J. Chinese Universities, 2019, 40: 719

[50] LingF, XiaoL, FangL, FengC, XieZ, LvY, ZhongW Org. Biomol. Chem., 2018, 16: 9274

[51] AnL T, CaiJ J, PanX Q, ChenT M, ZouJ P, ZhangW Tetrahedron Lett., 2015, 56: 3996

[52] XiaD, WangY, DuZ, ZhengQ Y, WangC Org. Lett., 2012, 14: 588

[53] HuangX, MaS Acc. Chem. Res., 2019, 52: 1301

[54] TaoX, WolkeC, DaniliucC G, KehrG, ErkerG Chem. Sci., 2019, 10: 2478

[55] ChenZ, DongV M Nat. Commun., 2017, 8: 784

[56] AlcaideB, AlmendrosP Chem. Soc. Rev., 2014, 43: 2886

[57] MaS, YuS Org. Lett., 2005, 7: 5063

[58] MunozM P, TorreM C D L, SierraM A Chem. Eur. J., 2012, 18: 4499

[59] MunozM P, TorreM C D L, SierraM A Adv. Synth. Catal., 2010, 352: 2189

[60] SunQ, DaniliucC G, BerganderK, KehrG, ErkerG J. Am. Chem. Soc., 2021, 143: 14992

[61] StephanD W J. Am. Chem. Soc., 2021, 143: 20002

[62] LégaréM A, PranckeviciusC, BraunschweigH Chem. Rev., 2019, 119: 8231

[63] XieF, HeJ, ZhangY Org. Chem. Front., 2023, 10: 3861

[64] LiuT, HeJ, ZhangY Chin. J. Chem., 2023, 41: 2446

[65] LiuT, YangM, HeJ, LiS, ZhangY Nat. Commun., 2023, 14: 703

[66] ZhangS, XuH, HeJ, ZhangY Adv. Synth. Catal., 2021, 363: 5319

[67] BasakS, MontoyaA A, WinfreyL, MelenR L, MorrillL C, PulisA P ACS Catal., 2020, 10: 4835

[68] StephanD W Chem, 2020, 6: 1520

[69] ZhangS, HanY, HeJ, ZhangY J. Org. Chem., 2018, 83: 1377

[70] HanY, ZhangS, HeJ, ZhangY J. Am. Chem. Soc., 2017, 139: 7399

[71] OestreichM, HermekeJ, MohrJ Chem. Soc. Rev., 2015, 44: 2202

[72] SongY, HeJ, ZhangY, GilsdorfR A, ChenE Y X Nat. Chem., 2023, 15: 366

[73] ZhaoW, WangQ, HeJ, ZhangY Macromol. Rapid Commun., 2022, 43: 2200088

[74] ZhaoW, HeJ, ZhangY Sci. Bull., 2019, 64: 1830

[75] BaiY, ZhangY Acta Polym. Sin., 2019, 50: 233

[76] HuL, ZhaoW, HeJ, ZhangY Molecules, 2018, 23: 665

[77] KeahlerT, MelenR L Cell Rep. Phys. Sci., 2021, 2: 100595

[78] ChenJ, ChenE Y X Angew. Chem. Int. Ed., 2015, 54: 6842

[79] Chen E. Y. X., e-Encycl. Reag. Org. Syn., 2012, DOI: https://doi.org/10.1002/047084289X.rn01382.

[80] ZhangY, MiyakeG M, JohnM G, FaliveneL, CaporasoL, CavalloL, ChenE Y X Dalton Trans., 2012, 41: 9119

[81] ChenE Y X Top. Curr. Chem., 2012, 334: 239

[82] XieF, HeJ, ZhangY ChemistrySelect, 2024, 9: e202400477

[83] LiuZ, TuX S, GuoL T, WangX C Chem. Sci., 2020, 11: 11548

[84] HanY, ZhangS, HeJ, ZhangY ACS Catal., 2018, 8: 8765

[85] LiC, ZhaoW, HeJ, ZhangY, ZhangW Angew. Chem. Int. Ed., 2022, 61: e202202448

[86] WanY, HeJ, ZhangY, ChenE Y X Angew. Chem. Int. Ed., 2022, 61: e202114946

[87] BaiY, WangH, HeJ, ZhangY, ChenE Y X Nat. Commun., 2021, 12: 4874

[88] BaiY, WangH, HeJ, ZhangY Angew. Chem. Int. Ed., 2020, 59: 11613

[89] BaiY, HeJ, ZhangY Angew. Chem. Int. Ed., 2018, 57: 17230

[90] WangQ, ZhaoW, ZhangS, HeJ, ZhangY, ChenE Y X ACS Catal., 2018, 8: 3571

[91] WangQ, ZhaoW, HeJ, ZhangY, ChenE Y X Macromolecules, 2017, 50: 123

[92] MaierA F G, TussingS, SchneiderT, FlörkeU, QuZ W, GrimmeS, ParadiesJ Angew. Chem. Int. Ed., 2016, 55: 12219

[93] HuangZ, YangX Q, YangF, LuT, ZhouQ Org. Lett., 2017, 19: 3524

[94] LuX, ZhuJ, HuangY Org. Lett., 2022, 24: 8816

[95] LehmannM, SchulzA, VillingerA Angew. Chem. Int. Ed., 2009, 48: 7444

[96] CeppiE, EckhardtW, GrobC A Tetrahedron Lett., 1973, 14: 3627

[97] ZhangY C, JiangF, ShiF Acc. Chem. Res., 2020, 53: 425

[98] ChengZ, LiM, ZhangX Y, SunY, YuQ L, ZhangX H, LuZ Angew. Chem. Int. Ed., 2023, 62: e202215029

[99] ChengZ, GuoJ, LuZ Chem. Commun., 2020, 56: 2229

[100] ZhuW R, SuQ, DengX Y, LiuJ S, ZhongT, MengS S, YiJ T, WengJ, LuG Chem. Sci., 2022, 13: 170

[101] GuoG, YuanY, BaoX, CaoX, SangT, WangJ, HuoC Org. Lett., 2021, 23: 6936

[102] YuanL, PalmieriA, PetriniM Adv. Synth. Catal., 2020, 362: 1509

[103] LingY, AnD, ZhouY Y, RaoW Org. Lett., 2019, 21: 3396

[104] PillaiyarT, UzairM, UllahS, SchnakenburgG, MüllerC E Adv. Synth. Catal., 2019, 361: 4286

[105] XiaoJ, WenH, WangL, XuL, HaoZ, ShaoC L, WangC Y Green Chem., 2016, 18: 1032

[106] LiD, WuT, LiangK, XiaC Org. Lett., 2016, 18: 2228

[107] ZhouM H, JiangY J, FanY S, GaoY, LiuS, ZhangS Q Org. Lett., 2014, 16: 1096

[108] SunF L, ZhengX J, GuQ, HeQ L, YouS L Eur. J. Org. Chem., 2010, 2010: 47

[109] YuH, YuZ Angew. Chem. Int. Ed., 2009, 48: 2929

[110] ZhangY, ZhangS X, FuL N, GuoQ X ChemCatChem., 2017, 9: 3107

[111] PathakT P, OsiakJ G, VadenR M, WelmB E, SigmanM S Tetrahedron, 2012, 68: 5203

[112] GuoX, PanS, LiuJ, LiZ J. Org. Chem., 2009, 74: 8848

[113] KaiserH M, LoW F, RiahiA M, SpannenbergA, BellerM, TseM K Org. Lett., 2006, 8: 5761

[114] ChakrabartyM, BasakR, GhoshN Tetrahedron Lett., 2001, 42: 3913

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