Solvent-free multi-component synthesis of unsymmetrical bis(indolyl)alkanes with Lewis acid-surfactant-SiO₂ as nanocatalyst

References

• Meckling, J.; Allan, B. B. The Evolution of Ideas in Global Climate Policy. Nat. Clim. Chang. 2020, 10, 434–438. DOI: 10.1038/s41558-020-0739-7.
   Web of Science ®Google Scholar
• Erythropel, H. C.; Zimmerman, J. B.; de Winter, T. M.; Petitjean, L.; Melnikov, F.; Lam, C. H.; Lounsbury, A. W.; Mellor, K. E.; Janković, N. Z.; Tu, Q.; et al. The Green ChemisTREE: 20 Years after Taking Root with the 12 Principles. Green Chem. 2018, 20, 1929–1961. DOI: 10.1039/C8GC00482J.
   Web of Science ®Google Scholar
• Zimmerman, J. B.; Anastas, P. T.; Erythropel, H. C.; Leitner, W. Designing for a Green Chemistry Future. Science. 2020, 367, 397–400. DOI: 10.1126/science.aay3060.
   PubMed Web of Science ®Google Scholar
• Tan, D.; Friščić, T. Mechanochemistry for Organic Chemists: An Update. Eur. J. Org. Chem. 2018, 2018, 18–33. DOI: 10.1002/ejoc.201700961.
   Web of Science ®Google Scholar
• Strukil, V. Synlett 2018, 29, 1281–1288. DOI: 10.1055/s-0036-1591868.
   Web of Science ®Google Scholar
• Friščić, T.; Mottillo, C.; Titi, H. M. Mechanochemistry for Synthesis. Angew. Chem. 2020, 132, 1030–1041. DOI: 10.1002/ange.201906755.
   Google Scholar
• Liu, Z.; Fan, G. P.;Wang, G. W. Unexpected Manganese(III) Acetate-Mediated Reactions of β-Enamino Carbonyl Compounds with 1-(Pyridin-2-yl)-Enones under Mechanical Milling Conditions. Chem. Commun. 2012, 48, 11665–11667. DOI: 10.1039/c2cc36360g.
   PubMed Web of Science ®Google Scholar
• Đud, M.; Briš, A.; Jušinski, I.; Gracin, D.; Margetić, D. Mechanochemical Friedel-Crafts Acylations. Beilstein. J. Org. Chem. 2019, 15, 1313–1320. DOI: 10.3762/bjoc.15.130.
   PubMed Web of Science ®Google Scholar
• Toda, F. Solid State Organic Chemistry: Efficient Reactions, Remarkable Yields, and Stereoselectivity. Acc. Chem. Res. 1995, 28, 480–486. DOI: 10.1021/ar00060a003.
   Web of Science ®Google Scholar
• Tanaka, K.; Toda, F. Solvent-Free Organic Synthesis. Chem. Rev. 2000, 100, 1025–1074. DOI: 10.1021/cr940089p.
   PubMed Web of Science ®Google Scholar
• Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Zolfigol, M. A.; Agheb, M.; Heydari, S. Silica Sulfuric Acid: An Efficient Reusable Heterogeneous Catalyst for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones in Water and under Solvent-Free Conditions. Catal. Commun. 2008, 9, 785–788. DOI: 10.1016/j.catcom.2007.08.019.
   Web of Science ®Google Scholar
• Xin, H. C.; Hu, L. N.; Yu, J. Q.; Sun, W. S.; An, Z. J. A Green Catalytic Method for Selective Synthesis of Iodophenols via Aerobic Oxyiodination under Organic Solvent-Free Conditions. Catal. Commun. 2017, 93, 1–4. DOI: 10.1016/j.catcom.2017.01.019.
   Web of Science ®Google Scholar
• Rodríguez, B.; Rantanen, T.; Bolm, C. Solvent-Free Asymmetric Organocatalysis in a Ball Mill. Angew. Chem. 2006, 118, 7078–7080. DOI: 10.1002/ange.200602820.
   Google Scholar
• Rodriguez, B.; Bruckmann, A.; Bolm, C. A Highly Efficient Asymmetric Organocatalytic Aldol Reaction in a Ball Mill. Chemistry. 2007, 13, 4710–4722. DOI: 10.1002/chem.200700188.
   PubMed Web of Science ®Google Scholar
• Bowmaker, G. A. Solvent-Assisted Mechanochemistry. Chem. Commun. 2013, 49, 334–348. DOI: 10.1039/c2cc35694e.
   PubMed Web of Science ®Google Scholar
• Bonnamour, J.; Métro, T. X.; Martinez, J.; Lamaty, F. Environmentally Benign Peptide Synthesis Using Liquid-Assisted Ball-Milling: Application to the Synthesis of Leu-Enkephalin. Green Chem. 2013, 15, 1116–1120. DOI: 10.1039/c3gc40302e.
   Web of Science ®Google Scholar
• Chen, L.; Regan, M.; Mack, J. The Choice is Yours: Using Liquid-Assisted Grinding to Choose between Products in the Palladium-Catalyzed Dimerization of Terminal Alkynes. ACS Catal. 2016, 6, 868–872. DOI: 10.1021/acscatal.5b02001.
   Web of Science ®Google Scholar
• Safe, S.; Papineni, S.; Chintharlapalli, S. Cancer Chemotherapy with Indole-3-Carbinol, Bis(3′-Indolyl)Methane and Synthetic Analogs. Cancer Lett. 2008, 269, 326–338. DOI: 10.1016/j.canlet.2008.04.021.
   PubMed Web of Science ®Google Scholar
• Sultana, N.; Arayne, M. S.; Rizvi, S. B. S.; Haroon, U.; Mesaik, M. A. Synthesis, Spectroscopic, and Biological Evaluation of Some Levofloxacin Metal Complexes. Med. Chem. Res. 2013, 22, 1371–1377. DOI: 10.1007/s00044-012-0132-9.
   Web of Science ®Google Scholar
• Bhattacharjee, P.; Boruah, P. K.; Das, M. R.; Bora, U. Direct C–H Bond Activation: Palladium-on-Carbon as a Reusable Heterogeneous Catalyst for C-2 Arylation of Indoles with Arylboronic Acids. New J. Chem. 2020, 44, 7675–7682. DOI: 10.1039/D0NJ00735H.
   Web of Science ®Google Scholar
• Veisi, H.; Maleki, B.; Eshbala, F. H.; Veisi, H.; Masti, R.; Ashrafi, S. S.; Baghayeri, M. In Situ Generation of Iron( Iii ) Dodecyl Sulfate as Lewis Acid-Surfactant Catalyst for Synthesis of Bis-Indolyl, Tris-Indolyl, Di(Bis-Indolyl), Tri(Bis-Indolyl), Tetra(Bis-Indolyl)Methanes and 3-Alkylated Indole Compounds in Water. RSC Adv. 2014, 4, 30683–30688. DOI: 10.1039/C4RA03194F.
   Web of Science ®Google Scholar
• Konwar, D.; Bora, U. Free Radical Triggered Convenient Synthesis of Bis(Indolyl)Methane with Potassium Peroxodisulfate as Catalyst. ChemistrySelect 2020, 5, 7460–7466. DOI: 10.1002/slct.202001776.
   Web of Science ®Google Scholar
• Bhattacharjee, P.; Bora, U. Molecular Iodine-Catalyzed Selective C-3 Benzylation of Indoles with Benzylic Alcohols: A Greener Approach toward Benzylated Indoles. Acs Omega. 2019, 4, 11770–11776. DOI: 10.1021/acsomega.9b01481.
   PubMed Web of Science ®Google Scholar
• He, F.; Li, P.; Gu, Y. L.; Li, G. X. Glycerol as a Promoting Medium for Electrophilic Activation of Aldehydes: Catalyst-Free Synthesis of di(Indolyl)Methanes, Xanthene-1,8(2H)-Diones and 1-Oxo-Hexahydroxanthenes. Green Chem. 2009, 11, 1767–1773. DOI: 10.1039/b916015a.
   Web of Science ®Google Scholar
• Zhang, Y. C.; Jiang, F.; Shi, F. Organocatalytic Asymmetric Synthesis of Indole-Based Chiral Heterocycles: Strategies, Reactions, and Outreach. Acc. Chem. Res. 2020, 53, 425–446. DOI: 10.1021/acs.accounts.9b00549.
   PubMed Web of Science ®Google Scholar
• Ling, Y.; An, D.; Zhou, Y. Y.; Rao, W. D. Ga(OTf)3-Catalyzed Temperature-Controlled Regioselective Friedel-Crafts Alkylation of Trifluoromethylated 3-Indolylmethanols with 2-Substituted Indoles: Divergent Synthesis of Trifluoromethylated Unsymmetrical 3,3′-and 3,6′-Bis(Indolyl)Methanes. Org. Lett. 2019, 21, 3396–3401. DOI: 10.1021/acs.orglett.9b01135.
   PubMed Web of Science ®Google Scholar
• He, Y. Y.; Sun, X. X.; Li, G. H.; Mei, G. J.; Shi, F. Substrate-Controlled Regioselective Arylations of 2-Indolylmethanols with Indoles: Synthesis of Bis(Indolyl)Methane and 3,3′-Bisindole Derivatives. J. Org. Chem. 2017, 82, 2462–2471. DOI: 10.1021/acs.joc.6b02850.
   PubMed Web of Science ®Google Scholar
• Chakrabarty, M.; Basak, R.; Ghosh, N. Microwave-Assisted Michael Reactions of 3-(2′-nitrovinyl)indole with indoles on TLC-grade silica gel. A new, facile synthesis of 2,2-bis(3′-indolyl)nitroethanes. Tetrahedron. Lett. 2001, 42, 3913–3915. DOI: 10.1016/S0040-4039(01)00581-0.
   Web of Science ®Google Scholar
• Muthukumar, A.; Rao, G. N.; Sekar, G. Zn(OTf)2-Catalyzed Access to Symmetrical and Unsymmetrical Bisindoles from α-Keto Amides. Org. Biomol. Chem. 2019, 17, 3921–3933. DOI: 10.1039/c9ob00114j.
   PubMed Web of Science ®Google Scholar
• Deb, M. L.; Deka, B.; Saikia, P. J.; Baruah, P. K. Base-Promoted Three-Component Cascade Approach to Unsymmetrical Bis(Indolyl)Methanes. Tetrahedron. Lett. 2017, 58, 1999–2003. DOI: 10.1016/j.tetlet.2017.04.032.
   Web of Science ®Google Scholar
• Xiao, J.; Wen, H.; Wang, L.; Xu, L. B.; Hao, Z. H.; Shao, C. L.; Wang, C. Y. Catalyst-Free Dehydrative S N 1-Type Reaction of Indolyl Alcohols with Diverse Nucleophiles “On Water”. Green Chem. 2016, 18, 1032–1037. DOI: 10.1039/C5GC01838B.
   Web of Science ®Google Scholar
• Lancianesi, S.; Palmieri, A.; Petrini, M. Synthesis and Functionalization of Unsymmetrical Arylsulfonyl Bisindoles and Bisbenzazoles. Adv. Synth. Catal. 2012, 354, 3539–3544. DOI: 10.1002/adsc.201200632.
   Web of Science ®Google Scholar
• Sarmah, D.; Bora, U. Methylene Surrogates for the Synthesis of 3,3′-Diindolylmethanes. ChemistrySelect. 2020, 5, 8577–8603. DOI: 10.1002/slct.202001694.
   Web of Science ®Google Scholar
• Wu, Z. Q.; Wang, G.; Yuan, S.; Wu, D.; Liu, W. Y.; Ma, B. J.; Bi, S. X.; Zhan, H. J.; Chen, X. Y. Synthesis of Bis(Indolyl)Methanes under Dry Grinding Conditions, Promoted by a Lewis Acid–Surfactant–SiO 2 -Combined Nanocatalyst. Green Chem. 2019, 21, 3542–3546. DOI: 10.1039/C9GC01073D.
   Web of Science ®Google Scholar
• Borpatra, P. J.; Deka, B.; Rajbongshi, B. K.; Deb, M. L.; Baruah, P. K. One-Pot Sequential Multi-Component Reaction: Synthesis of 3-Substituted Indoles. Synthetic. Commun. 2018, 48, 2074–2082. DOI: 10.1080/00397911.2018.1482352.
   Web of Science ®Google Scholar
• Hunter, L. The C-F Bond as a Conformational Tool in Organic and Biological Chemistry. Beilstein. J. Org. Chem. 2010, 6, 38–38. DOI: 10.3762/bjoc.6.38.
   PubMed Web of Science ®Google Scholar