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Synthesis 2009(7): 1137-1146  
DOI: 10.1055/s-0028-1088003
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium Supported on a Polyionic Resin as an Efficient, Ligand-Free, and Recyclable Catalyst for Heck, Suzuki-Miyaura, and Sonogashira Reactions

Basudeb Basu*a, Sajal Dasa, Pralay Dasa, Bablee Mandala, Dipanjan Banerjeeb, Fredrik Almqvist*b
a Department of Chemistry, University of North Bengal, Darjeeling 734013, India
Fax: +91(353)2699001; e-Mail: basu_nbu@hotmail.com;
b Department of Chemistry, Umeå University, 91087 Umeå, Sweden
e-Mail: Fredrik.Almqvist@chem.umu.se;
Further Information

Publication History

Received 27 November 2008
Publication Date:
06 March 2009 (online)

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Abstract

Polyionic Amberlite resin formate (ARF), derived from commercially available Amberlite resin chloride by simple rinsing with aqueous formic acid, could be soaked with palladium(0) from palladium salts, the formate counteranion being the reducing source. The resulting Amberlite resin formate supported with palladium(0), ARF-Pd, showed excellent catalytic activity in Heck, Suzuki­-Miyaura, and Sonogashira couplings with a range of substrates. The catalyst may be recovered easily and quantitatively without leaching and recycled; it was tested for five runs without any significant loss of activity.

Key words

Amberlite resin - C-C coupling - heterogeneous catalysis - palladium

    References

  • 1a Organopalladium Chemistry for Organic Synthesis   Negishi E.-I. Wiley-Interscience; New York: 2002. 
  • 1b Metal-Catalyzed Cross-Coupling Reactions   de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. 
  • 1c Mauger CC. Mignani GA. Aldrichimica Acta  2006,  39:  17 
    Search in Google Scholar
  • 1d Yin L. Liebscher J. Chem. Rev.  2007,  107:  133 
    Search in Google Scholar
  • 1e Herrmann WA. Öfele K. Preysing DV. Schneider SK. J. Organomet. Chem.  2003,  687:  229 
    Search in Google Scholar
  • 2a Miyaura N. Adv. Metal-Org. Chem.  1998,  6:  187 
    Search in Google Scholar
  • 2b Tietze LF. Kettschau G. Heuschert U. Nordman G. Chem. Eur. J.  2001,  7:  368 
    Search in Google Scholar
  • For review on recent applications of Suzuki-Miyaura coupling and biaryl formation:
  • 3a Kotha S. Lahiri K. Kashinath D. Tetrahedron  2002,  58:  9633 
    Search in Google Scholar
  • 3b Alberico D. Scott ME. Lautens M. Chem. Rev.  2007,  107:  174 
    Search in Google Scholar
  • For review on Heck coupling, see:
  • 3c Beletskaya IP. Cheprakov AV. Chem. Rev.  2000,  100:  3009 
    Search in Google Scholar
  • 4a Nicolaou KC. Li H. Boddy CNC. Ramanjulu JM. Yue T.-Y. Natarajan S. Chu X.-J. Brase S. Rubsam F. Chem. Eur. J.  1999,  5:  2584 
    Search in Google Scholar
  • 4b Kamikawa K. Watanabe T. Daimon A. Uemura M. Tetrahedron  2000,  56:  2325 
    Search in Google Scholar
  • 4c Haberli A. Leumann CJ. Org. Lett.  2001,  3:  489 
    Search in Google Scholar
  • 5a Applied Homogeneous Catalysis   Cornils B. Herrmann WA. Wiley-VCH; Weinheim: 1998. 
  • 5b Blaser H.-U. Indolese A. Schnyder A. Steiner H. Studer M. J. Mol. Catal. A: Chem.  2001,  173:  3 
    Search in Google Scholar
  • 5c Nicolaou KC. Koumbis AE. Takayanagi M. Natarajan S. Jain NF. Bando T. Li H. Hughes R. Chem. Eur. J.  1999,  5:  2622 
    Search in Google Scholar
  • 5d Reetz MT. Wastermann E. Angew. Chem. Int. Ed.  2000,  39:  165 
    Search in Google Scholar
  • 5e Zapf A. Beller M. Chem. Eur. J.  2001,  7:  2908 
    Search in Google Scholar
  • 6a Schwarz J. Böhm VPW. Gardiner MG. Grosche M. Herrmann WA. Heiringer W. Raudaschl-Seiber G. Chem. Eur. J.  2000,  6:  1773 
    Search in Google Scholar
  • 6b Yin L. Liebscher J. Chem. Rev.  2007,  107:  133 
    Search in Google Scholar
  • 6c Nam N.-H. Sardari S. Parang K. J. Comb. Chem.  2003,  5:  480 
    Search in Google Scholar
  • 6d Biffis A. Zecca M. Basato M. J. Mol. Catal. A: Chem.  2001,  173:  249 
    Search in Google Scholar
  • 6e Zhou J. Zhou R. Mo L. Zhou S. Zheng X. J. Mol. Catal. A: Chem.  2002,  178:  289 
    Search in Google Scholar
  • 6f See a special issue edited by Gladysz JA. Chem. Rev.  2002,  102:  3215 
    Search in Google Scholar
  • 6g Ley SV. Baxendale IR. Bream RN. Jackson PS. Leach AG. Longbottom DA. Nesi M. Scott JS. Storer I. Taylor SJ. J. Chem. Soc., Perkin Trans. 1  2000,  3815 
  • 7a Herrmann WA. Brosner C. Ofele K. Beller M. Fischer H. J. Mol. Catal. A: Chem.  1995,  103:  133 
    Search in Google Scholar
  • 7b Beller M. Fischer H. Kuhlein K. Reisinger CP. Herrmann WA. J. Organomet. Chem.  1996,  520:  257 
    Search in Google Scholar
  • 7c Garrett CE. Prasad K. Adv. Synth. Catal.  2004,  346:  889 
    Search in Google Scholar
  • 8a Proch S. Mei Y. Villanueva JMR. Lu Y. Karpov A. Ballauff M. Kempe R. Adv. Synth. Catal.  2008,  350:  493 
    Search in Google Scholar
  • 8b Tsvelikhovsky D. Blum J. Eur. J. Org. Chem.  2008,  2417 
  • 9a Eisenstadt A. In Utilization of the Heterogeneous Palladium-on-Carbon Catalyzed Heck Reaction in Applied Synthesis   Vol. 1:  Herkes FE. Marcel Dekker; Basel: 1998.  p.415-427  
    Search in Google Scholar
  • 9b Zhang Z. Wang Z. J. Org. Chem.  2006,  71:  7485 
    Search in Google Scholar
  • 9c Zhao F. Bhanage BM. Shirai M. Arai M. Chem. Eur. J.  2000,  6:  843 
    Search in Google Scholar
  • 9d Kabalka GW. Namboodiri V. Wang L. Chem. Commun.  2001,  775 
  • 9e Sakurai H. Tsukuda T. Hirao T. J. Org. Chem.  2002,  67:  2721 
    Search in Google Scholar
  • 9f Tagata T. Nishida M. J. Org. Chem.  2003,  68:  9412 
    Search in Google Scholar
  • 9g Gruber M. Chouzier S. Köhler K. Djakovitch L. Appl. Catal., A  2004,  265:  161 
    Search in Google Scholar
  • 9h Mizukoshi Y. Makise Y. Shuto T. Hu J. Tominaga A. Shironita S. Tanabe S. Ultrason. Sonochem.  2007,  14:  387 
    Search in Google Scholar
  • 10a Pawelec B. Mariscal R. Navarro RM. van Bokhorst S. Rojas S. Fierro JLG. Appl. Catal., A.  2002,  225:  223 
    Search in Google Scholar
  • 10b Mehendale NC. Sietsma JRA. de Jong KP. van Walree CA. Gebbink RJMK. van Koten G. Adv. Synth. Catal.  2007,  349:  2619 
    Search in Google Scholar
  • 10c Saffarzadeh-Matin S. Kerton FM. Lynam JM. Rayner CM. Green Chem.  2006,  8:  965 
    Search in Google Scholar
  • 10d Li H. Wang L. Li P. Synthesis  2007,  1635 
  • 10e Bernini R. Cacchi S. Fabrizi G. Forte G. Niembro S. Petrucci F. Pleixats R. Prastaro A. Sebastián RM. Soler R. Tristany M. Vallribera A. Org. Lett.  2008,  10:  561 
    Search in Google Scholar
  • 10f Niembro S. Shafir A. Vallribera A. Alibés R. Org. Lett.  2008,  10:  3215 
    Search in Google Scholar
  • 11a Ren N. Yang Y.-H. Zhang Y.-H. Wang Q.-R. Tang Y. J. Catal.  2007,  246:  215 
    Search in Google Scholar
  • 11b Corma A. Garcia H. Leyva A. Primo A. Appl. Catal., A  2003,  247:  41 
    Search in Google Scholar
  • 11c Artok L. Bulut H. Tetrahedron Lett.  2004,  45:  3881 
    Search in Google Scholar
  • 11d Pröckl SS. Kleist W. Gruber MA. Köhler K. Angew. Chem. Int. Ed.  2004,  43:  1881 
    Search in Google Scholar
  • 12 Mehnert CP. Weaver DW. Ying JY. J. Am. Chem. Soc.  1998,  120:  12289 
    CrossrefSearch in Google Scholar
  • 13 Bennur TH. Ramani A. Bal R. Chanda BM. Sivasankar S. Catal. Commun.  2002,  3:  493 
    CrossrefSearch in Google Scholar
  • 14a Corma A. Garcia H. Leyva A. Primo A. Appl. Catal., A: Gen.  2004,  257:  77 
    Search in Google Scholar
  • 14b Shimizu K. Kan-no T. Kodama T. Hagiwara H. Kitayama Y. Tetrahedron Lett.  2002,  43:  5653 
    Search in Google Scholar
  • 14c Shimizu K. Maruyama R. Komai S. Kodama T. Kitayama Y. J. Catal.  2004,  227:  202 
    Search in Google Scholar
  • For selected examples:
  • 15a Bergbreiter DE. Osburn PL. Liu Y.-S. J. Am. Chem. Soc.  1999,  121:  9531 
    Search in Google Scholar
  • 15b Uozumi Y. Danjo H. Hayashi T. J. Org. Chem.  1999,  64:  3384 
    Search in Google Scholar
  • 15c Shieh W.-C. Shekhar R. Blacklock T. Tedesco A. Synth. Commun.  2002,  32:  1059 
    Search in Google Scholar
  • 15d McNamara CA. King F. Bradley M. Tetrahedron Lett.  2004,  45:  8239 
    Search in Google Scholar
  • 15e Cammidge AN. Baines NJ. Bellingham RK. Chem. Commun.  2001,  2588 
  • 15f Yamada YMA. Takeda K. Takahashi H. Ikegami S. Org. Lett.  2002,  4:  3371 
    Search in Google Scholar
  • 15g Yamada YMA. Takeda K. Takahashi H. Ikegami S. J. Org. Chem.  2003,  68:  7733 
    Search in Google Scholar
  • For reviews:
  • 16a Moreno-Mañas M. Pleixats R. Acc. Chem. Res.  2003,  36:  638 
    Search in Google Scholar
  • 16b Roucoux A. Schulz J. Patin H. Chem. Rev.  2002,  102:  3757 
    Search in Google Scholar
  • 16c Zhang M. Zhang W. J. Phys. Chem. C  2008,  112:  6245 
    Search in Google Scholar
  • 17a Choudary BM. Madhi S. Chowdari NS. Kantam ML. Sreedhar B. J. Am. Chem. Soc.  2002,  124:  14127 
    Search in Google Scholar
  • 17b Astruc D. Lu F. Aranzaes JR. Angew. Chem. Int. Ed.  2005,  44:  7852 ; Angew. Chem. 2005, 117, 8062
    Search in Google Scholar
  • 17d Wu L. Li B.-L. Huang Y.-Y. Zhou H.-F. He Y.-M. Fan Q.-H. Org. Lett.  2006,  8:  3605 
    Search in Google Scholar
  • 18a Ramarao C. Ley SV. Smith SC. Shirley IM. De Almerda N. Chem. Commun.  2002,  1132 
  • 18b Yu JQ. Wu HC. Ramarao C. Spencer JB. Ley SV. Chem. Commun.  2003,  678 
  • 18c Ley SV. Mitchell C. Pears D. Ramarao C. Yu JQ. Zhou W. Org. Lett.  2003,  5:  4665 
    Search in Google Scholar
  • 18d Chechik V. Crooks RM. J. Am. Chem. Soc.  2000,  122:  1243 
    Search in Google Scholar
  • 18e Kobayashi S. Nagayama S. J. Am. Chem. Soc.  1998,  120:  2985 
    Search in Google Scholar
  • 18f Kobayashi S. Endo M. Nagayama S. J. Am. Chem. Soc.  1999,  121:  11229 
    Search in Google Scholar
  • 18g Akiyama R. Kobayashi S. Angew. Chem. Int. Ed.  2001,  40:  3469 
    Search in Google Scholar
  • 18h Akiyama R. Kobayashi S. Angew. Chem. Int. Ed.  2002,  41:  2602 
    Search in Google Scholar
  • 19a Akiyama R. Kobayashi S. J. Am. Chem. Soc.  2003,  125:  3412 
    Search in Google Scholar
  • 19b Okamota K. Akiyama R. Kobayashi S. J. Org. Chem.  2004,  69:  2871 
    Search in Google Scholar
  • 19c Okamota K. Akiyama R. Kobayashi S. Org. Lett.  2004,  6:  1987 
    Search in Google Scholar
  • 19d Okamota K. Akiyama R. Yoshida H. Yoshida T. Kobayashi S. J. Am. Chem. Soc.  2005,  127:  2125 
    Search in Google Scholar
  • 19e Hagio H. Sugiura M. Kobayashi S. Org. Lett.  2006,  8:  375 
    Search in Google Scholar
  • 20a Strimbu L. Liu J. Kaifer AE. Langmuir  2003,  19:  483 
    Search in Google Scholar
  • 20b Rahim EH. Kamounah FS. Frederiksen J. Christensen JB. Nano Lett.  2001,  1:  499 
    Search in Google Scholar
  • 20c Pittelkow M. Moth-Poulsen K. Boas U. Christensen JB. Langmuir  2003,  19:  7682 
    Search in Google Scholar
  • 20d Garcia-Martinez JC. Lezutekong R. Crooks RM. J. Am. Chem. Soc.  2005,  127:  5097 
    Search in Google Scholar
  • 21 Basu B. Das S. Das P. Nanda AK. Tetrahedron Lett.  2005,  46:  8591 
    CrossrefSearch in Google Scholar
  • 22a For reviews: Benaglia M. Puglisi A. Cozzi F. Chem. Rev.  2003,  103:  3401 
    Search in Google Scholar
  • 22b Kirschning A. Monenschein H. Wittenberg R. Angew. Chem. Int. Ed.  2001,  40:  650 
    Search in Google Scholar
  • For examples of scavenging metals by ion-exchange resins and catalysis:
  • 23a Thiot C. Schmutz M. Wagner A. Mioskowski C. Angew. Chem. Int. Ed.  2006,  45:  2868 
    Search in Google Scholar
  • 23b Kirschning A. Jas G. Top. Curr. Chem.  2004,  242:  209 
    Search in Google Scholar
  • 23c Jas G. Kirschning A. Chem. Eur. J.  2003,  9:  5708 
    Search in Google Scholar
  • 23d Solodenko W. Wen H. Leue S. Stuhlmann F. Argirusi GS. Jas G. Schonfeld H. Kunz U. Kirschning A. Eur. J. Org. Chem.  2004,  3601 
  • 24 Basu B. Bhuiyan MdMH. Das P. Hossain I. Tetrahedron Lett.  2003,  44:  8931 
    CrossrefSearch in Google Scholar
  • 25 Choudary BM. Madhi S. Kantam ML. Sreedhar B. Iwasawa Y. J. Am. Chem. Soc.  2004,  126:  2292 
    CrossrefPubMedSearch in Google Scholar
  • 26 Basu B. Das P. Bhuiyan MdMH. Jha S. Tetrahedron Lett.  2003,  44:  3817 
    CrossrefSearch in Google Scholar
  • For selected examples:
  • 27a Miguez JMA. Adrio LM. Sousa-Pedrares A. Vila JM. Hii KK. J. Org. Chem.  2007,  72:  7771 
    Search in Google Scholar
  • 27b Conreaux D. Bossharth E. Monteiro N. Desbordes P. Vors JP. Balme G. Org. Lett.  2007,  9:  271 
    Search in Google Scholar
  • 27c Č erňa I. Pohl R. Klepetářvá B. Hocek M. Org. Lett.  2006,  8:  5389 
    Search in Google Scholar
  • 27d Beletskaya IP. Tsvetkov AV. Latyshev GV. Lukashev NV. Russ. J. Org. Chem.  2003,  39:  1660 
    Search in Google Scholar
  • 28a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett.  1975,  16:  4467 
    Search in Google Scholar
  • 28b Sonogashira K. In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pergamon Press; Oxford: 1999.  p.521 
    Search in Google Scholar
  • 28c Wu JS. Watson MD. Zhang L. Wang ZH. Mullen K. J. Am. Chem. Soc.  2004,  126:  177 
    Search in Google Scholar
  • 28d Hennrich G. Echavarren AM. Tetrahedron Lett.  2004,  45:  1147 
    Search in Google Scholar
  • 28e Wilson JN. Josowicz M. Wang YQ. Bunz UHF. Chem. Commun.  2003,  2962 
  • 28f Li CC. Xie ZX. Zhang YD. Chen JH. Yang Z. J. Org. Chem.  2003,  68:  8500 
    Search in Google Scholar
  • 28g Tsang KY. Brimble MA. Bremner JB. Org. Lett.  2003,  5:  4425 
    Search in Google Scholar
  • 28h Paterson I. Davies RDM. Heimann AL. Maquez R. Meyer A. Org. Lett.  2003,  5:  4477 
    Search in Google Scholar
  • 28i Lane JW. Halcomb RL. Org. Lett.  2003,  5:  4017 
    Search in Google Scholar
  • 28j Hansen TM. Engler MM. Forsyth CJ. Bioorg. Med. Chem. Lett.  2003,  13:  2127 
    Search in Google Scholar
  • 28k Ohyaba N. Nishkawa T. Isobe M. J. Am. Chem. Soc.  2003,  125:  8798 
    Search in Google Scholar
  • 28l Marshall JA. Schaaf GM. J. Org. Chem.  2003,  68:  7428 
    Search in Google Scholar
  • 28m Lopez S. Fernandeztrillo F. Castedo L. Saa C. Org. Lett.  2003,  5:  3275 
    Search in Google Scholar
  • 29a Feuerstein M. Doucet H. Santelli M. Tetrahedron Lett.  2004,  45:  1603 
    Search in Google Scholar
  • 29b Heuzé K. Méry D. Gauss D. Astruc D. Chem. Commun.  2003,  2274 
  • 29c Méry D. Heuzé K. Astruc D. Chem. Commun.  2003,  1934 
  • 29d Soheili A. Albaneze-Walker J. Murry JA. Dormer PG. Hughes DL. Org. Lett.  2003,  5:  4191 
    Search in Google Scholar
  • 29e Mas-Marzá E. Segarra AM. Claver C. Peris E. Fernandez E. Tetrahedron Lett.  2003,  44:  6595 
    Search in Google Scholar
  • 29f Leadbeater NE. Tominack BJ. Tetrahedron Lett.  2003,  44:  8653 
    Search in Google Scholar
  • 30a Wang L. Li P. Zhang Y. Chem. Commun.  2004,  514 
  • 30b Beletskaya IP. Latyshev GV. Tsvetkov AV. Lukashev NV. Tetrahedron Lett.  2003,  44:  5011 
    Search in Google Scholar
  • 31 Dams M. Drijkoningen L. Pauwels B. Van Tendeloo G. De Vos DE. Jacobs PA. J. Catal.  2002,  209:  225 
    CrossrefSearch in Google Scholar
  • 32 Lee D.-H. Kim J.-H. Jun B.-H. Kang H. Park J. Lee Y.-S. Org. Lett.  2008,  10:  1609 
    CrossrefPubMedSearch in Google Scholar
  • 33 Encyclopedia of Reagents for Organic Synthesis   Vol. 4:  John Wiley & Sons; Chichester: 1992.  p.2301 
  • 34 France H. Heilbron IM. Hey DH. J. Chem. Soc.  1939,  1288 
    Crossref
  • 35 Dictionary of Organic Compounds   Chapman and Hall; London: 1982.  5th ed.. p.5119 
  • 36 Dictionary of Organic Compounds   Chapman and Hall; London: 1987.  5th ed., Suppl. 5. p.270 
  • 37 Modena G. Rivetti F. Tonellato U. J. Org. Chem.  1978,  43:  1521 
    CrossrefSearch in Google Scholar