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Boric acid Catalyzed efficient Synthesis of Dipyrromethanes in Water

Author Affiliations

  • 1 DB College, Department of Chemistry, University of Delhi, Delhi, INDIA

Res.J.chem.sci., Volume 4, Issue (10), Pages 58-62, October,18 (2014)


A simple and efficient methodology has been demonstrated for the synthesis of dipyrromethanes. Boric acid catalyzed condensation of two equivalent of pyrrole with one equivalent of aldehyde gives dipyrromethane in good yield at room temperature in aqueous medium.


  1. Temelli B. and Unaleroglu C., Synthesis of meso-tetraphenyl porphyrins via condensation of dipyrromethanes with N-tosyl imines, Tetrahedron, 65,2043-2050 (2009)
  2. Gale P.A., Anzenbacher P. Jr. and Sessler J.L., Calixpyrroles II, Coord. Chem. Rev.,222, 57-102 (2001)
  3. Zhan H.-Y., Liu H.-Y., Chen H.-J. and Jiang H.-F., Preparation of meso-substituted trans-AB-corroles in ionic liquids, Tetrahedron Lett.,50, 2196-2199 (2009)
  4. Drain C.M., Hupp J.T., Suslick K.S., Wasielewski M.R. and Chen X., A perspective on four new porphyrin-based functional materials and devices, J. Porphyrins Phthalocyanines, 6, 243-258 (2002)
  5. Okura I., overview of optical sensors using porphyrins, J. Porphyrins Phthalocyanines,6, 268-270 (2002)
  6. (a) Sternberg E.D., Dolphin D. and Bruckner C., Porphyrin-based photosensitizers for use in photodynamic therapy, Tetrahedron, 54, 4151-4202 (1998); (b) Macdonald I.J. and Dougherty T.J., Basic principles of photodynamic therapy, J Porphyrins Phthalocyanines, 5,105-129 (2001)
  7. (a) Ganesan M., Lalonde M.P., Gambarotta S. and Yap G.P.A., Isolation and Characterization of Linear Polymeric {[1,1-H10-CN) Sm[Na(THF)]: A 30-Electron Species with a (-Cp)Ln type Structure, organometallics,20, 2443-2445 (2001); (b) Gao G., korobkov I. and Gambarotta S., Divalent Molybdenum Complexes of the Dipyrrolide Ligand System, Isolation of a Mo Unit with a 45 Twist Angle, Inorg. Chem., 43, 1108-1115 (2004)
  8. (a) Milgrom L. R. and Yahioglu G., Trans-disubstituted meso-tetraethynylporphyrins, Tetrahedron Lett., 37, 4069- 4072 (1996); (b) Lee C. H. and Lindsey J.S., One-flask synthesis of meso-substituted dipyrromethanes and their application in the synthesis of trans-substituted porphyrin building blocks, Tetrahedron, 50, 11427-11440 (1994)
  9. Bruno G., Cafeo G., Kohnke F. H. and Nicol F., Tuning the anion binding propertiesof calixpyrroles by meansof p-nitrophenyl substituents at their meso-positions, Tetrahedron, 63, 10003-10010 (2007)
  10. Mizutani T., Ema T., Tomita T., Kuroda Y. andogoshi H., Design and Synthesis of a Trifunctional Chiral Porphyrin with C Symmetry as a Chiral Recognition Host for Amino Acid Esters, J. Am. Chem. Soc.,116, 4240- 4250 (1994)
  11. Gao G.-H., Lu L., Gao J.-B., Zhou W.-J., Yang J.-G., Yu X.-Y. and He M.-Y., One-step Synthesis of Dipyrromethanes in the Presenceof Ionic Liquid [Hmim] BF, Chinese Chem. Lett.,16, 900-902 (2005)
  12. Sobral A.J.F.N., Rebanda N.G.C.L., Silva M.d., Lampreia S.H., Silva M. R., Beja A.M., Paixao J. A. and Gonsalves A.M. dA. R.,one-step synthesis of dipyrromethanes in water, Tetrahedron Lett.,44, 39713973 (2003)
  13. Okitsuo., Suzuki R. and Kobayashi S., Efficient Synthesis of Piperidine Derivatives. Development of Metal Triflate-Catalyzed Diastereoselective Nucleophilic Substitution Reactions of 2-Methoxy- and 2-Acyloxypiperidines, Chem., 66, 809-823 (2001)
  14. Tundo P., Anastas P., Black D.S., Breen J., Collins T., Memoli S., Miyamoto J., Polyakoff M. and Tumas W., Synthetic pathways and processes in green chemistry. Introductory overview, Pure Appl. Chem., 72, 1207-1232 (2000)
  15. Simon M.O. and Li C.J., Green chemistry oriented organic synthesis in water, Chem. Soc. Rev.,41, 1415-1427 (2012)
  16. Nguyen T.B., Sorres J., Tran M.Q., Ermolenko L. and Mourabit A.A., Boric Acid: A Highly Efficient Catalyst for Transamidation of Carboxamides with Amines, org. Lett., 14, 3202-3205 (2012)
  17. Chaudhuri M.K., Hussain S., Kantam M.L. and Neelima B., Boric acid: a novel and safe catalyst for aza-Michael reactions in water, Tetrahedron Lett., 46, 8329-8331 (2005)
  18. Chaudhuri M.K. and Hussain S., Boric acid catalyzed thia-Michael reactions in wateror alcohols, J. Mol. Catal. A: Chem., 269, 214-217 (2007)
  19. Tu S., Fang F., Miao C., Jiang H., Feng Y., Shi D. and Wang X., One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using boric acid as catalyst, Tetrahedron Lett., 44, 6153-6155 (2003)
  20. Kumar A., Saxena D. and Gupta M.K., Boric acid catalyzed Ugi three-component reaction in aqueous media RSC Advances, 3, 4610-4612 (2013)
  21. Laha J.K., Dhanalekshmi S., Taniguchi M., Ambroise A. and Lindsey J.S., A Scalable Synthesis of Meso-Substituted Dipyrromethanes,org. Process Research & Development, 7, 799-812 (2003)
  22. (a) Ali S.S., Molecular iodine- catalyzed convenient synthesis of meso substituted Dipyrromethanes, Arch. Appl. Sci. Res., 2, 121-125 (2010); (b) Qasim S.S. and Ali S.S., A novel method for the synthesis of meso substituted dipyrromethanes, Int. J. Appl. Biol. Pharma. Tech.,2, 301-306 (2011)
  23. (a) Rao P.D., Littler B.J., Geier G.R. III and Lindsey J.S., Efficient Synthesis of Monoacyl Dipyrromethanes and Their Use in the Preparation of Sterically Unhindered trans-Porphyrins, Chem.,65, 1084-1092 (2000)
  24. (a) Geier G. R. III and Lindsey J. S., Investigation of porphyrin-forming reactions. Part 2. Examination of the reaction course in two-step, one-flask syntheses of meso-substituted porphyrins, J. Chem. Soc., Perkin Trans. 2,687-700 (2001); (b) Geier G. R. III and Lindsey J. S., Effects of diverse acid catalystson the reaction course in the two-stepone-flask synthesis of meso-tetraphenylporphyr in, J. Porphyrins Phthalocyanines, 6,159-185 (2002)