Triphenylphosphine-m-sulfonate/carbon tetrabromide as an efficient and easily recoverable catalyst system for friedelcrafts alkylation of indoles with carbonyl compounds or acetals

ACS Sustainable Chemistry and Engineering

Volumn 1, Issue 5, 2013, Pages 549-553

  Huo, Congde ^a   Sun, Chougu ^a   Wang, Cheng ^a   Jia, Xiaodong ^a   Chang, Wenju ^a  

^a NORTHWEST NORMAL UNIVERSITY   (China)

Author keywords

Carbonyl compounds; Crafts alkylation; Friedel; Indoles; Recoverable catalyst

Indexed keywords

CARBON TETRABROMIDE; FRIEDEL; FRIEDEL-CRAFTS ALKYLATION; INDOLES; RECOVERABLE AND REUSABLE CATALYST; RECOVERABLE CATALYSTS;

ALKYLATION; CATALYSTS;

CARBONYL COMPOUNDS;

EID: 84880262548     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400033t     Document Type: Article

References (34)

1. Friedel, C.; Crafts, J. M. A new general synthetical method of producing hydrocarbons. J. Chem. Soc. 1877, 32, 725.
2. Rueping, M.; Nachtsheim, B. J. A review of new developments in the Friedel-Crafts alkylation: From green chemistry to asymmetric catalysis. Beilstein J. Org. Chem. 2010, 6, 6.
3. Bandini, M.; Tragni, M. Pi-activated alcohols: An emerging class of alkylating agents for catalytic Friedel-Crafts reactions. Org. Biomol. Chem. 2009, 7, 1501.
4. Poulsen, T. B.; Joørgensen, K. A. Catalytic asymmetric Friedel-Crafts alkylation reactions: Copper showed the way. Chem. Rev. 2008, 108, 2903.
5. Huo, C.; Xu, X.; An, J.; Jia, X.; Wang, X.; Wang, C. Approach to construct polysubstituted 1,2-dihydronaphtho[2,1-b]furans and their aerobic oxidative aromatization. J. Org. Chem. 2012, 77, 8310.
6. Huo, C.; Xu, X.; Jia, X.; Wang, X.; An, J.; Sun, C. Friedel-Crafts alkylation between chalcone epoxides and heteroarenes induced by rriarylaminium salt. Tetrahedron 2012, 68, 190.
7. Huo, C.; An, J.; Xu, X.; Jia, X.; Wang, X.; Kang, L. Tandem reaction between chalcone epoxides and 2-naphthyl ethers to construct complex naphtho[2,1-b]furans. Tetrahedron Lett. 2013, 54, 1145.
8. Nicolaou, K. C.; Reingruber, R.; Sarlah, D.; Brase, S. Enantioselective intramolecular Friedel-Crafts-Type -arylation of aldehydes. J. Am. Chem. Soc. 2009, 131, 2086.
9. Stadler, D.; Bach, T. Concise stereoselective synthesis of (-)-podophyllotoxin by an intermolecular iron(III)-catalyzed Friedel-Crafts alkylation. Angew. Chem., Int. Ed. 2008, 47, 7557.
10. Mertins, K.; Iovel, I.; Kischel, J.; Zapf, A.; Beller, M. Transitionmetal-catalyzed benzylation of arenes and heteroarenes. Angew. Chem., Int. Ed. 2004, 44, 238.
11. Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Bisand trisindolylmethanes (BIMs and TIMs). Chem. Rev. 2010, 110, 2250.
12. Fischer, H. E. Ueber einige Reactionen der Indole. Chem. Ber. 1886, 19, 2988.
13. Tayebee, R.; Nehzat, F.; Rezaei-Seresht, E.; Mohammadi, F. Z.; Rafieeb, E. An efficient and green synthetic protocol for the preparation of bis(indolyl)methanes catalyzed by H6P2W18O6224H2O, with emphasis on the catalytic proficiency of Wells-Dawson versus Keggin heteropolyacids. J. Mol. Catal. A: Chem. 2011, 351, 154.
14. Deb, M. L.; Bhuyan, P. J. An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature. Tetrahedron Lett. 2006, 47, 1441.
15. Bandgar, B. P.; Shaikh, K. A. Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions. Tetrahedron Lett. 2003, 44, 1959.
16. Cornils, B.; Kuntz, E. G. Introducing TPPTS and related ligands for industrial biphasic processes. J. Organomet. Chem. 1995, 502, 177.
17. Huo, C.; Chan, T. H. A novel liquid-phase strategy for organic synthesis using organic ions as soluble supports. Chem. Soc. Rev. 2010, 39, 2977.
18. Huo, C.; He, X.; Chan, T. H. Zwitterionic phosphonium sulfonates as easily phase-separable ion-tagged Wittig reagents. J. Org. Chem. 2008, 73, 8583.
19. Huo, C.; Chan, T. H. Carbon tetrabromide/sodium triphenylphosphine-m- sulfonate (TPPMS) as an efficient and easily recoverable catalyst for acetalization and tetrahydropyranylation reactions. Adv. Synth. Catal. 2009, 351, 1933.
20. Osawa, T.; Namiki, M. Structure elucidation of streptindole, a novel genotoxic metabolite isolated from intestinal bacteria. Tetrahedron Lett. 1983, 24, 4719.
21. Chakrabarty, M.; Basak, R.; Harigaya, Y. A Sojourn in the synthesis and bioactivity of diindolylalkanes. Heterocycles 2001, 55, 2431.
22. Hogan I. T.; Sainsbury, M. An efficient synthesis of streptindole. Synthesis 1984, 872.
23. Bartoli, G.; Bosco, M.; Foglia, G.; Giuliani, A.; Marcantoni, E.; Sambri, L. Solvent-free indoles addition to carbonyl compounds promoted by CeCl37H2O-NaI-SiO2: An efficient method for the synthesis of streptindole. Synthesis 2004, 895.
24. Sosnovskikh, V. Y.; Irgashev, R. A. Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: synthesis of (chromon-3-yl)bis(indol-3-yl) methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones under solvent-free conditions. Tetrahedron Lett. 2007, 48, 7436.
25. Sosnovskikh, V. Y.; Irgashev, R. A.; Levchenko, A. Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: synthesis and some reactions of (chromon-3-yl)bis(indol-3-yl)-methanes and E-2-hydroxy-3-(1- methylpyrrol-2-ylmethylene)-chroman-4-ones. Tetrahedron 2008, 64, 6607.
26. Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S.-I. Scandium(III) triflate-catalyzed Friedel-Crafts alkylation reactions. J. Org. Chem. 1997, 62, 6997.
27. Fukuzawa, S.-I.; Tsuchimoto, T.; Hiyama, T. Superacidcatalyzed reductive Friedel-Crafts reaction of arenes using arenecarbaldehyde acetals. J. Org. Chem. 1997, 62, 151.
28. Kubczyk, T. M.; Williams, S. M.; Kean, J. R.; Davies, T. E.; Taylor, S. H.; Graham, A. E. Nanoporous aluminosilicate catalyzed Friedel-Crafts alkylation reactions of indoles with aldehydes and acetals. Green Chem. 2011, 13, 2320.
29. Azizian, J.; Thimouri, F.; Mohammadizadeh, F. M. Ammonium chloride catalyzed one-pot synthesis of diindolylmethanes under solvent-free conditions. Catal. Commun. 2007, 8, 1117.
30. Tanaka, K.; Toda, F. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025.
31. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesisA review. Tetrahedron 2001, 57, 9225.
32. Loupy A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. New solvent-free organic synthesis using focused microwaves. Synthesis 1998, 1213.
33. Mendoza, A.; Ishihara, Y.; Baran, P. S. Scalable enantioselective total synthesis of taxanes. Nature Chem. 2012, 4, 21.
34. Wernerova M.; Hudlicky, T. On the practical limits of determining isolated product yields and ratios of stereoisomers: reflections, analysis, and redemption. Synlett 2010, 2701.