Download PDF
Synthesis 2011(7): 1125-1131  
DOI: 10.1055/s-0030-1258452
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Phosphine-Free Heck Reaction in Water Using Pd(l-Proline)2 as the Catalyst Under Microwave Irradiation

Bharat Kumar Allam, Krishna Nand Singh*
Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi-221005, India
Fax: +91(542)2368127; e-Mail: knsinghbhu@yahoo.co.in;
Further Information

Publication History

Received 3 December 2010
Publication Date:
01 March 2011 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

The present report describes an efficient and simple protocol for phosphine-free Heck reactions in water using a Pd(l-proline)2 complex as the catalyst under controlled microwave irradiation conditions. This methodology is versatile and provides excellent yields of products in short reaction times and minimizes costs, operational hazards and environmental pollution.

Key words

Heck reaction - palladium - Pd(l-proline)2 - microwave irradiation - phosphine-free

    References

  • 1 Heck RF. Acc. Chem. Res.  1979,  12:  146 
    CrossrefSearch in Google Scholar
  • 2a Heck RF. Palladium Reagents in Organic Synthesis   Academic Press; London: 1985. 
  • 2b Heck RF. In Comprehensive Organic Synthesis   Vol 4:  Trost BM. Fleming I. Pergamon; New York: 1991.  Chap. 4.3.
    Search in Google Scholar
  • 2c Negishi E.-I. Handbook of Organopalladium Chemistry for Organic Synthesis   Wiley; New York: 2002. 
  • 2d Tsuji J. Palladium Reagents and Catalysts   Wiley; Chichester: 1995. 
  • 2e The Mizoroki-Heck Reaction   Oestreich M. Wiley; Chichester: 2009. 
  • 2f Alonso F. Beletskaya IP. Yus M. Tetrahedron  2005,  61:  11771 
    Search in Google Scholar
  • 2g Beletskaya IP. Cheprakov AV. Coord. Chem. Rev.  2004,  2337 
  • 3a de Meijere A. Diederich F. Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  Wiley-VCH; Weinheim: 2004. 
    Search in Google Scholar
  • 3b Whitcombe NJ. Hii KK. Gibson SE. Tetrahedron  2001,  57:  7449 
    Search in Google Scholar
  • 4a de Vries JG. Can. J. Chem.  2001,  79:  1086 
    Search in Google Scholar
  • 4b Blaser H.-U. Indolese A. Schnyder A. Steiner H. Studer M. J. Mol. Catal. A: Chem.  2001,  173:  3 
    Search in Google Scholar
  • 4c Tucker CE. de Vries JG. Top. Catal.  2002,  19:  111 
    Search in Google Scholar
  • 4d de Vries JG. de Vries AHM. Eur. J. Org. Chem.  2003,  799 
  • 4e Blaser H.-U. Indolese A. Naud F. Nettekoven U. Schnyder A. Adv. Synth. Catal.  2004,  346:  1583 
    Search in Google Scholar
  • 5a Littke AF. Fu GC. J. Org. Chem.  1999,  64:  10 
    Search in Google Scholar
  • 5b Littke AF. Fu GC. J. Am. Chem. Soc.  2001,  123:  6989 
    Search in Google Scholar
  • 5c Shaughnessy KH. Kim P. Hartwig JF. J. Am. Chem. Soc.  1999,  121:  2123 
    Search in Google Scholar
  • 5d Ehrentraut A. Zapf A. Beller M. Synlett  2000,  1589 
  • 5e Bohm VPW. Herrmann WA. Chem. Eur. J.  2000,  6:  1017 
    Search in Google Scholar
  • 6a Herrmann WA. Brossmer C. Oefele K. Reisinger C.-P. Priermeier T. Beller M. Fischer H. Angew. Chem., Int. Ed. Engl.  1995,  34:  1844 
    Search in Google Scholar
  • 6b Herrmann WA. Brossmer C. Reisinger C.-P. Priermeier TH. Oefele K. Beller M. Chem. Eur. J.  1997,  3:  1357 
    Search in Google Scholar
  • 6c Ohff M. Ohff A. van der Boom ME. Milstein D. J. Am. Chem. Soc.  1997,  119:  11687 
    Search in Google Scholar
  • 6d Shaw BL. Perera SD. Staley EA. Chem. Commun.  1998,  1361 
  • 6e Albisson DA. Bedford RB. Scully PN. Lawrence SE. Chem. Commun.  1998,  2095 
  • 6f Miyazaki F. Yamaguchi K. Shibasaki M. Tetrahedron Lett.  1998,  39:  7379 
    Search in Google Scholar
  • 6g Morales-Morales D. Redón R. Yung C. Jensen CM. Chem. Commun.  2000,  1619 
  • 6h Bedford RB. Welch SL. Chem. Commun.  2001,  129 
  • 6i Gibson S. Foster DF. Eastam GR. Tooze RP. Cole-Hamilton DJ. Chem. Commun.  2001,  779 
  • 7a Ohff M. Ohff A. Milstein D. Chem. Commun.  1999,  357 
  • 7b Iyer S. Ramesh C. Tetrahedron Lett.  2000,  41:  8981 
    Search in Google Scholar
  • 7c Gai X. Grigg R. Ramzan MI. Sridharan V. Collard S. Muir JE. Chem. Commun.  2000,  2053 
  • 7d Alonso DA. Nájera C. Pacheco MC. Org. Lett.  2000,  2:  1823 
    Search in Google Scholar
  • 7e Munoz MP. Martin-Matute B. Fernández-Rivas C. Cárdenas DJ. Echavarren AM. Adv. Synth. Catal.  2001,  343:  338 
    Search in Google Scholar
  • 7f Beletskaya IP. Kashin AN. Karlstedt NB. Mitin AV. Cheprakov AV. Kazankov GM. J. Organomet. Chem.  2001,  622:  89 
    Search in Google Scholar
  • 7g Alonso DA. Nájera C. Pacheco MC. Adv. Synth. Catal.  2002,  344:  172 
    Search in Google Scholar
  • 7h Rocaboy C. Gladysz JA. Org. Lett.  2002,  4:  1993 
    Search in Google Scholar
  • 7i Consorti CS. Zanini ML. Leal S. Ebeling G. Dupont J. Org. Lett.  2003,  5:  983 
    Search in Google Scholar
  • 8a Gruber AS. Zim D. Ebeling G. Monteriro AL. Dupont J. Org. Lett.  2000,  2:  1287 
    Search in Google Scholar
  • 8b Bergbreiter DE. Osburn PL. Wilson A. Sink E. J. Am. Chem. Soc.  2000,  122:  9058 
    Search in Google Scholar
  • 9a Bourissou D. Guerret O. Gabaï FP. Bertrand G. Chem. Rev.  2000,  100:  39 
    Search in Google Scholar
  • 9b Herrmann WA. Angew. Chem. Int. Ed.  2002,  41:  1290 
    Search in Google Scholar
  • 10 Yang C. Lee HM. Nolan SP. Org. Lett.  2001,  3:  1511 
    CrossrefPubMedSearch in Google Scholar
  • 11 Yao Q. Kinney EP. Yang Z. J. Org. Chem.  2003,  68:  7528 
    CrossrefSearch in Google Scholar
  • 12a Jeffery T. In Advances in Metal-Organic Chemistry   Vol. 5:  Liebeskind LS. JAI Press; Greenwich: 1996.  p.153 
    Search in Google Scholar
  • 12b Bohm VPW. Herrmann WA. Chem. Eur. J.  2000,  6:  1017 
    Search in Google Scholar
  • 12c Dupont J. Pfeffer M. Spencer J. Eur. J. Inorg. Chem.  2001,  1917 
  • 12d Biffis A. Zecca M. Basato M. J. Mol. Catal. A: Chem.  2001,  173:  249 
    Search in Google Scholar
  • 12e Kohler K. Heidenreich RG. Krauter JGE. Pietsch J. Chem. Eur. J.  2002,  8:  622 
    Search in Google Scholar
  • 12f Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Search in Google Scholar
  • 12g van der Boom ME. Milstein D. Chem. Rev.  2003,  103:  1759 
    Search in Google Scholar
  • 12h Bedford RB. Chem. Commun.  2003,  1787 
  • 12i Beletskaya IP. Cheprakov AV. J. Organomet. Chem.  2004,  689:  4055 
    Search in Google Scholar
  • 12j Peris E. Crabtree RH. Coord. Chem. Rev.  2004,  248:  2239 
    Search in Google Scholar
  • 12k Christmann U. Vilar R. Angew. Chem. Int. Ed.  2005,  44:  366 
    Search in Google Scholar
  • 13a Reetz MT. Breinbauer R. Wanninger K. Tetrahedron Lett.  1996,  37:  4099 
    Search in Google Scholar
  • 13b Beller M. Fischer H. Kühlein K. Reisinger C.-P. Herrmann WA. J. Organomet. Chem.  1996,  520:  257 
    Search in Google Scholar
  • 13c Reetz MT. Westermann E. Angew. Chem. Int. Ed.  2000,  39:  165 
    Search in Google Scholar
  • 13d Reetz MT. de Vries JG. Chem. Commun.  2004,  1559 
  • 14a Deshmukh RR. Rajagopal R. Srinivasan KV. Chem. Commun.  2001,  1544 
  • 14b de Vries AHM. Mulders JMCA. Mommers JHM. Henderickx HJW. de Vries JG. Org. Lett.  2003,  5:  3285 
    Search in Google Scholar
  • 14c Eberhard MR. Org. Lett.  2004,  6:  2125 
    Search in Google Scholar
  • 15a Reetz MT. Westermann E. Angew. Chem. Int. Ed.  2000,  39:  165 
    Search in Google Scholar
  • 15b Sengupta S. Bhattacharyya S. Tetrahedron Lett.  1995,  36:  4475 
    Search in Google Scholar
  • 15c Crisp GT. Gebauer MG. Tetrahedron  1996,  52:  12465 
    Search in Google Scholar
  • 15d Desmazeau P. Legros J.-Y. Fiaud J.-C. Tetrahedron Lett.  1998,  39:  6707 
    Search in Google Scholar
  • 15e Reetz MT. Lohmer G. Schwickardi R. Angew. Chem. Int. Ed.  1998,  37:  481 
    Search in Google Scholar
  • 15f Reetz MT. Westermann E. Lohmer R. Lohmer G. Tetrahedron Lett.  1998,  39:  8449 
    Search in Google Scholar
  • 15g Bråthe A. Gundersen L.-L. Rise F. Eriksen AB. Vollsnes AV. Wang L. Tetrahedron  1999,  55:  211 
    Search in Google Scholar
  • 15h Carmichael AJ. Earle MJ. Holbrey JD. McCormac PB. Seddon KR. Org. Lett.  1999,  1:  997 
    Search in Google Scholar
  • 15i de Vries AHM. Parlevliet FJ. Schmieder-van de Vondervoort L. Mommers JHM. Henderickx HJW. Walet MAM. de Vries JG. Adv. Synth. Catal.  2002,  344:  996 
    Search in Google Scholar
  • 15j Okubo K. Shirai M. Yokoyama C. Tetrahedron Lett.  2002,  43:  7115 
    Search in Google Scholar
  • 15k Chandrasekhar S. Narsihmulu C. Sultana SS. Reddy NR. Org. Lett.  2002,  4:  4399 
    Search in Google Scholar
  • 16a Li C.-H. Chan T.-H. Organic Reactions in Aqueous Media   John Wiley & Sons; New York: 1997. 
  • 16b Cornils B. Herrmann WA. Aqueous Phase Organometallic Chemistry: Concepts and Applications   Wiley-VCH; Weinheim: 1998. 
  • 16c Organic Synthesis in Water   Grieco PA. Blackie Academic & Professional; London: 1998. 
  • 16d Joo F. Aqueous Organometallic Catalysis   Kluwer; Dordrecht: 2001. 
  • 17a Metal Catalysis in Water   Grieco PA. Blackie Academic & Professional; London: 1998. 
  • 18a Sinou D. Top. Curr. Chem.  1999,  206:  41 
    Search in Google Scholar
  • 18b Genet JP. Savignac M. J. Organomet. Chem.  1999,  576:  305 
    Search in Google Scholar
  • 19a Botella L. Nájera C. Tetrahedron Lett.  2004,  45:  1833 
    Search in Google Scholar
  • 19b Mukhopadhyay S. Rothenberg G. Joshi A. Baidossi M. Sasson Y. Adv. Synth. Catal.  2002,  344:  348 
    Search in Google Scholar
  • 19c Uozumi Y. Kimura T. Synlett  2002,  2045 
  • 20 Adam D. Nature  2003,  421:  571 
    CrossrefSearch in Google Scholar
  • 21a Gedye R. Smith F. Westaway K. Ali H. Baldisera L. Laberge L. Rousel R. Tetrahedron Lett.  1986,  27:  279 
    Search in Google Scholar
  • 21b Giguere RJ. Bary TL. Duncan SM. Majetich G. Tetrahedron Lett.  1986,  27:  4945 
    Search in Google Scholar
  • 22a Loupy A. Microwaves in Organic Synthesis   2nd ed.:  Wiley-VCH; Weinheim: 2002. 
    Search in Google Scholar
  • 22b Hayes BL. Microwave Synthesis: Chemistry at the Speed of Light   CEM Publishing; Matthews (NC): 2002. 
  • 22c Lidstrom P. Tierney JP. Microwave-Assisted Organic Synthesis   Blackwell Scientific; Oxford: 2005. 
  • 22d Kappe CO. Stadler A. Microwaves in Organic and Medicinal Chemistry   Wiley-VCH; Weinheim: 2005. 
  • 22e Kappe CO. Dallinger DS. Murphree S. Practical Microwave Synthesis for Organic Chemists: Strategies, Instruments, and Protocols   Wiley-VCH; Weinheim: 2009. 
  • 23a Bose AK. Manhas MS. Banik BK. Robb EW. Res. Chem. Intermed.  1994,  20:  1 
    Search in Google Scholar
  • 23b Caddick S. Tetrahedron  1995,  51:  10403 
    Search in Google Scholar
  • 23c Galema SA. Chem. Soc. Rev.  1997,  26:  233 
    Search in Google Scholar
  • 23d Lidström P. Fierney J. Wathey B. Westman J. Tetrahedron  2001,  57:  9225 
    Search in Google Scholar
  • 23e Kappe CO. Angew. Chem. Int. Ed.  2004,  43:  6250 
    Search in Google Scholar
  • 23f Hayes BL. Aldrichimica Acta  2004,  37:  66 
    Search in Google Scholar
  • 23g Roberts BA. Strauss CR. Acc. Chem. Res.  2005,  38:  653 
    Search in Google Scholar
  • 24a Anastas PT. Warner JC. Green Chemistry: Theory and Practice   Oxford University Press; New York: 2000. 
  • 24b Anastas PT. Williamson TC. Green Chemistry: Frontiers in Benign Chemical Synthesis and Process   Oxford University Press; New York: 1998. 
  • 25a Dallinger D. Kappe CO. Chem. Rev.  2007,  107:  2563 
    Search in Google Scholar
  • 25b Razzaq T. Kappe CO. ChemSusChem  2008,  1:  123 
    Search in Google Scholar
  • 25c Varma RS. Green Chem.  2008,  10:  1129 
    Search in Google Scholar
  • 26a De la Hoz A. Díaz-Ortíz A. Moreno A. Curr. Org. Chem.  2004,  8:  903 
    Search in Google Scholar
  • 26b Langa F. De la Cruz P. De la Hoz A. Díaz-Ortíz A. Díez-Barra E. Contemp. Org. Synth.  1997,  4:  373 
    Search in Google Scholar
  • 27a Raghuvanshi DS. Singh KN. Synlett  2011,  373 
  • 27b Raghuvanshi DS. Singh KN. ARKIVOC  2010,  (x):  305 
    Search in Google Scholar
  • 27c Singh KN. Singh SK. ARKIVOC  2009,  (xiii):  153 
    Search in Google Scholar
  • 27d Singh SK. Singh KN. J. Heterocycl. Chem.  2010,  47:  194 
    Search in Google Scholar
  • 28 Pottabathula S. Keesara S. Likhar PR. Balsubramanian S. Kakita VM. Bhargava S. Mannepalli LK. J. Organomet. Chem.  2011,  696:  795 
    CrossrefSearch in Google Scholar
  • 29 Yuan D.-Y. Tu Y.-Q. Fan C.-A. J. Org. Chem.  2008,  73:  7797 
    CrossrefSearch in Google Scholar
  • 30 Modak A. Mondal J. Aswal VK. Bhaumik A. J. Mater. Chem.  2010,  20:  8099 
    CrossrefSearch in Google Scholar
  • 31 Dong D.-J. Li H.-H. Tian S.-K. J. Am. Chem. Soc.  2010,  132:  5018 
    CrossrefSearch in Google Scholar
  • 32 Denmark SE. Edwards MG. J. Org. Chem.  2006,  71:  7293 
    CrossrefSearch in Google Scholar