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

Basudeb Basu; Sajal Das; Pralay Das; Bablee Mandal; Dipanjan Banerjee; Fredrik Almqvist

doi:10.1055/s-0028-1088003

PAPER

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 Das^a, Pralay Das^a, Bablee Mandal^a, Dipanjan Banerjee^b, 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;

Abstract

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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

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References

<A NAME="RZ25908SS-1A">1a</A> Organopalladium Chemistry for Organic Synthesis Negishi E.-I. Wiley-Interscience; New York: 2002.

<A NAME="RZ25908SS-1B">1b</A> Metal-Catalyzed Cross-Coupling Reactions de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.

<A NAME="RZ25908SS-1C">1c</A> Mauger CC. Mignani GA. Aldrichimica Acta 2006, 39: 17

<A NAME="RZ25908SS-1D">1d</A> Yin L. Liebscher J. Chem. Rev. 2007, 107: 133

<A NAME="RZ25908SS-1E">1e</A> Herrmann WA. Öfele K. Preysing DV. Schneider SK. J. Organomet. Chem. 2003, 687: 229

<A NAME="RZ25908SS-2A">2a</A> Miyaura N. Adv. Metal-Org. Chem. 1998, 6: 187

<A NAME="RZ25908SS-2B">2b</A> Tietze LF. Kettschau G. Heuschert U. Nordman G. Chem. Eur. J. 2001, 7: 368

For review on recent applications of Suzuki-Miyaura coupling and biaryl formation:

<A NAME="RZ25908SS-3A">3a</A> Kotha S. Lahiri K. Kashinath D. Tetrahedron 2002, 58: 9633

<A NAME="RZ25908SS-3B">3b</A> Alberico D. Scott ME. Lautens M. Chem. Rev. 2007, 107: 174

For review on Heck coupling, see:

<A NAME="RZ25908SS-3C">3c</A> Beletskaya IP. Cheprakov AV. Chem. Rev. 2000, 100: 3009

<A NAME="RZ25908SS-4A">4a</A> 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

<A NAME="RZ25908SS-4B">4b</A> Kamikawa K. Watanabe T. Daimon A. Uemura M. Tetrahedron 2000, 56: 2325

<A NAME="RZ25908SS-4C">4c</A> Haberli A. Leumann CJ. Org. Lett. 2001, 3: 489

<A NAME="RZ25908SS-5A">5a</A> Applied Homogeneous Catalysis Cornils B. Herrmann WA. Wiley-VCH; Weinheim: 1998.

<A NAME="RZ25908SS-5B">5b</A> Blaser H.-U. Indolese A. Schnyder A. Steiner H. Studer M. J. Mol. Catal. A: Chem. 2001, 173: 3

<A NAME="RZ25908SS-5C">5c</A> Nicolaou KC. Koumbis AE. Takayanagi M. Natarajan S. Jain NF. Bando T. Li H. Hughes R. Chem. Eur. J. 1999, 5: 2622

<A NAME="RZ25908SS-5D">5d</A> Reetz MT. Wastermann E. Angew. Chem. Int. Ed. 2000, 39: 165

<A NAME="RZ25908SS-5E">5e</A> Zapf A. Beller M. Chem. Eur. J. 2001, 7: 2908

<A NAME="RZ25908SS-6A">6a</A> Schwarz J. Böhm VPW. Gardiner MG. Grosche M. Herrmann WA. Heiringer W. Raudaschl-Seiber G. Chem. Eur. J. 2000, 6: 1773

<A NAME="RZ25908SS-6B">6b</A> Yin L. Liebscher J. Chem. Rev. 2007, 107: 133

<A NAME="RZ25908SS-6C">6c</A> Nam N.-H. Sardari S. Parang K. J. Comb. Chem. 2003, 5: 480

<A NAME="RZ25908SS-6D">6d</A> Biffis A. Zecca M. Basato M. J. Mol. Catal. A: Chem. 2001, 173: 249

<A NAME="RZ25908SS-6E">6e</A> Zhou J. Zhou R. Mo L. Zhou S. Zheng X. J. Mol. Catal. A: Chem. 2002, 178: 289

<A NAME="RZ25908SS-6F">6f</A> See a special issue edited by Gladysz JA. Chem. Rev. 2002, 102: 3215

<A NAME="RZ25908SS-6G">6g</A> 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

<A NAME="RZ25908SS-7A">7a</A> Herrmann WA. Brosner C. Ofele K. Beller M. Fischer H. J. Mol. Catal. A: Chem. 1995, 103: 133

<A NAME="RZ25908SS-7B">7b</A> Beller M. Fischer H. Kuhlein K. Reisinger CP. Herrmann WA. J. Organomet. Chem. 1996, 520: 257

<A NAME="RZ25908SS-7C">7c</A> Garrett CE. Prasad K. Adv. Synth. Catal. 2004, 346: 889

<A NAME="RZ25908SS-8A">8a</A> Proch S. Mei Y. Villanueva JMR. Lu Y. Karpov A. Ballauff M. Kempe R. Adv. Synth. Catal. 2008, 350: 493

<A NAME="RZ25908SS-8B">8b</A> Tsvelikhovsky D. Blum J. Eur. J. Org. Chem. 2008, 2417

<A NAME="RZ25908SS-9A">9a</A> 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

<A NAME="RZ25908SS-9B">9b</A> Zhang Z. Wang Z. J. Org. Chem. 2006, 71: 7485

<A NAME="RZ25908SS-9C">9c</A> Zhao F. Bhanage BM. Shirai M. Arai M. Chem. Eur. J. 2000, 6: 843

<A NAME="RZ25908SS-9D">9d</A> Kabalka GW. Namboodiri V. Wang L. Chem. Commun. 2001, 775

<A NAME="RZ25908SS-9E">9e</A> Sakurai H. Tsukuda T. Hirao T. J. Org. Chem. 2002, 67: 2721

<A NAME="RZ25908SS-9F">9f</A> Tagata T. Nishida M. J. Org. Chem. 2003, 68: 9412

<A NAME="RZ25908SS-9G">9g</A> Gruber M. Chouzier S. Köhler K. Djakovitch L. Appl. Catal., A 2004, 265: 161

<A NAME="RZ25908SS-9H">9h</A> Mizukoshi Y. Makise Y. Shuto T. Hu J. Tominaga A. Shironita S. Tanabe S. Ultrason. Sonochem. 2007, 14: 387

<A NAME="RZ25908SS-10A">10a</A> Pawelec B. Mariscal R. Navarro RM. van Bokhorst S. Rojas S. Fierro JLG. Appl. Catal., A. 2002, 225: 223

<A NAME="RZ25908SS-10B">10b</A> Mehendale NC. Sietsma JRA. de Jong KP. van Walree CA. Gebbink RJMK. van Koten G. Adv. Synth. Catal. 2007, 349: 2619

<A NAME="RZ25908SS-10C">10c</A> Saffarzadeh-Matin S. Kerton FM. Lynam JM. Rayner CM. Green Chem. 2006, 8: 965

<A NAME="RZ25908SS-10D">10d</A> Li H. Wang L. Li P. Synthesis 2007, 1635

<A NAME="RZ25908SS-10E">10e</A> 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

<A NAME="RZ25908SS-10F">10f</A> Niembro S. Shafir A. Vallribera A. Alibés R. Org. Lett. 2008, 10: 3215

<A NAME="RZ25908SS-11A">11a</A> Ren N. Yang Y.-H. Zhang Y.-H. Wang Q.-R. Tang Y. J. Catal. 2007, 246: 215

<A NAME="RZ25908SS-11B">11b</A> Corma A. Garcia H. Leyva A. Primo A. Appl. Catal., A 2003, 247: 41

<A NAME="RZ25908SS-11C">11c</A> Artok L. Bulut H. Tetrahedron Lett. 2004, 45: 3881

<A NAME="RZ25908SS-11D">11d</A> Pröckl SS. Kleist W. Gruber MA. Köhler K. Angew. Chem. Int. Ed. 2004, 43: 1881

<A NAME="RZ25908SS-12">12</A> Mehnert CP. Weaver DW. Ying JY. J. Am. Chem. Soc. 1998, 120: 12289

<A NAME="RZ25908SS-13">13</A> Bennur TH. Ramani A. Bal R. Chanda BM. Sivasankar S. Catal. Commun. 2002, 3: 493

<A NAME="RZ25908SS-14A">14a</A> Corma A. Garcia H. Leyva A. Primo A. Appl. Catal., A: Gen. 2004, 257: 77

<A NAME="RZ25908SS-14B">14b</A> Shimizu K. Kan-no T. Kodama T. Hagiwara H. Kitayama Y. Tetrahedron Lett. 2002, 43: 5653

<A NAME="RZ25908SS-14C">14c</A> Shimizu K. Maruyama R. Komai S. Kodama T. Kitayama Y. J. Catal. 2004, 227: 202

For selected examples:

<A NAME="RZ25908SS-15A">15a</A> Bergbreiter DE. Osburn PL. Liu Y.-S. J. Am. Chem. Soc. 1999, 121: 9531

<A NAME="RZ25908SS-15B">15b</A> Uozumi Y. Danjo H. Hayashi T. J. Org. Chem. 1999, 64: 3384

<A NAME="RZ25908SS-15C">15c</A> Shieh W.-C. Shekhar R. Blacklock T. Tedesco A. Synth. Commun. 2002, 32: 1059

<A NAME="RZ25908SS-15D">15d</A> McNamara CA. King F. Bradley M. Tetrahedron Lett. 2004, 45: 8239

<A NAME="RZ25908SS-15E">15e</A> Cammidge AN. Baines NJ. Bellingham RK. Chem. Commun. 2001, 2588

<A NAME="RZ25908SS-15F">15f</A> Yamada YMA. Takeda K. Takahashi H. Ikegami S. Org. Lett. 2002, 4: 3371

<A NAME="RZ25908SS-15G">15g</A> Yamada YMA. Takeda K. Takahashi H. Ikegami S. J. Org. Chem. 2003, 68: 7733

For reviews:

<A NAME="RZ25908SS-16A">16a</A> Moreno-Mañas M. Pleixats R. Acc. Chem. Res. 2003, 36: 638

<A NAME="RZ25908SS-16B">16b</A> Roucoux A. Schulz J. Patin H. Chem. Rev. 2002, 102: 3757

<A NAME="RZ25908SS-16C">16c</A> Zhang M. Zhang W. J. Phys. Chem. C 2008, 112: 6245

<A NAME="RZ25908SS-17A">17a</A> Choudary BM. Madhi S. Chowdari NS. Kantam ML. Sreedhar B. J. Am. Chem. Soc. 2002, 124: 14127

<A NAME="RZ25908SS-17B">17b</A> Astruc D. Lu F. Aranzaes JR. Angew. Chem. Int. Ed. 2005, 44: 7852 ; Angew. Chem. 2005, 117, 8062

<A NAME="RZ25908SS-17D">17d</A> Wu L. Li B.-L. Huang Y.-Y. Zhou H.-F. He Y.-M. Fan Q.-H. Org. Lett. 2006, 8: 3605

<A NAME="RZ25908SS-18A">18a</A> Ramarao C. Ley SV. Smith SC. Shirley IM. De Almerda N. Chem. Commun. 2002, 1132

<A NAME="RZ25908SS-18B">18b</A> Yu JQ. Wu HC. Ramarao C. Spencer JB. Ley SV. Chem. Commun. 2003, 678

<A NAME="RZ25908SS-18C">18c</A> Ley SV. Mitchell C. Pears D. Ramarao C. Yu JQ. Zhou W. Org. Lett. 2003, 5: 4665

<A NAME="RZ25908SS-18D">18d</A> Chechik V. Crooks RM. J. Am. Chem. Soc. 2000, 122: 1243

<A NAME="RZ25908SS-18E">18e</A> Kobayashi S. Nagayama S. J. Am. Chem. Soc. 1998, 120: 2985

<A NAME="RZ25908SS-18F">18f</A> Kobayashi S. Endo M. Nagayama S. J. Am. Chem. Soc. 1999, 121: 11229

<A NAME="RZ25908SS-18G">18g</A> Akiyama R. Kobayashi S. Angew. Chem. Int. Ed. 2001, 40: 3469

<A NAME="RZ25908SS-18H">18h</A> Akiyama R. Kobayashi S. Angew. Chem. Int. Ed. 2002, 41: 2602

<A NAME="RZ25908SS-19A">19a</A> Akiyama R. Kobayashi S. J. Am. Chem. Soc. 2003, 125: 3412

<A NAME="RZ25908SS-19B">19b</A> Okamota K. Akiyama R. Kobayashi S. J. Org. Chem. 2004, 69: 2871

<A NAME="RZ25908SS-19C">19c</A> Okamota K. Akiyama R. Kobayashi S. Org. Lett. 2004, 6: 1987

<A NAME="RZ25908SS-19D">19d</A> Okamota K. Akiyama R. Yoshida H. Yoshida T. Kobayashi S. J. Am. Chem. Soc. 2005, 127: 2125

<A NAME="RZ25908SS-19E">19e</A> Hagio H. Sugiura M. Kobayashi S. Org. Lett. 2006, 8: 375

<A NAME="RZ25908SS-20A">20a</A> Strimbu L. Liu J. Kaifer AE. Langmuir 2003, 19: 483

<A NAME="RZ25908SS-20B">20b</A> Rahim EH. Kamounah FS. Frederiksen J. Christensen JB. Nano Lett. 2001, 1: 499

<A NAME="RZ25908SS-20C">20c</A> Pittelkow M. Moth-Poulsen K. Boas U. Christensen JB. Langmuir 2003, 19: 7682

<A NAME="RZ25908SS-20D">20d</A> Garcia-Martinez JC. Lezutekong R. Crooks RM. J. Am. Chem. Soc. 2005, 127: 5097

<A NAME="RZ25908SS-21">21</A> Basu B. Das S. Das P. Nanda AK. Tetrahedron Lett. 2005, 46: 8591

<A NAME="RZ25908SS-22A">22a</A> For reviews: Benaglia M. Puglisi A. Cozzi F. Chem. Rev. 2003, 103: 3401

<A NAME="RZ25908SS-22B">22b</A> Kirschning A. Monenschein H. Wittenberg R. Angew. Chem. Int. Ed. 2001, 40: 650

For examples of scavenging metals by ion-exchange resins and catalysis:

<A NAME="RZ25908SS-23A">23a</A> Thiot C. Schmutz M. Wagner A. Mioskowski C. Angew. Chem. Int. Ed. 2006, 45: 2868

<A NAME="RZ25908SS-23B">23b</A> Kirschning A. Jas G. Top. Curr. Chem. 2004, 242: 209

<A NAME="RZ25908SS-23C">23c</A> Jas G. Kirschning A. Chem. Eur. J. 2003, 9: 5708

<A NAME="RZ25908SS-23D">23d</A> Solodenko W. Wen H. Leue S. Stuhlmann F. Argirusi GS. Jas G. Schonfeld H. Kunz U. Kirschning A. Eur. J. Org. Chem. 2004, 3601

<A NAME="RZ25908SS-24">24</A> Basu B. Bhuiyan MdMH. Das P. Hossain I. Tetrahedron Lett. 2003, 44: 8931

<A NAME="RZ25908SS-25">25</A> Choudary BM. Madhi S. Kantam ML. Sreedhar B. Iwasawa Y. J. Am. Chem. Soc. 2004, 126: 2292

<A NAME="RZ25908SS-26">26</A> Basu B. Das P. Bhuiyan MdMH. Jha S. Tetrahedron Lett. 2003, 44: 3817

For selected examples:

<A NAME="RZ25908SS-27A">27a</A> Miguez JMA. Adrio LM. Sousa-Pedrares A. Vila JM. Hii KK. J. Org. Chem. 2007, 72: 7771

<A NAME="RZ25908SS-27B">27b</A> Conreaux D. Bossharth E. Monteiro N. Desbordes P. Vors JP. Balme G. Org. Lett. 2007, 9: 271

<A NAME="RZ25908SS-27C">27c</A> Č erňa I. Pohl R. Klepetářvá B. Hocek M. Org. Lett. 2006, 8: 5389

<A NAME="RZ25908SS-27D">27d</A> Beletskaya IP. Tsvetkov AV. Latyshev GV. Lukashev NV. Russ. J. Org. Chem. 2003, 39: 1660

<A NAME="RZ25908SS-28A">28a</A> Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 16: 4467

<A NAME="RZ25908SS-28B">28b</A> Sonogashira K. In Comprehensive Organic Synthesis Vol. 3: Trost BM. Fleming I. Pergamon Press; Oxford: 1999. p.521

<A NAME="RZ25908SS-28C">28c</A> Wu JS. Watson MD. Zhang L. Wang ZH. Mullen K. J. Am. Chem. Soc. 2004, 126: 177

<A NAME="RZ25908SS-28D">28d</A> Hennrich G. Echavarren AM. Tetrahedron Lett. 2004, 45: 1147

<A NAME="RZ25908SS-28E">28e</A> Wilson JN. Josowicz M. Wang YQ. Bunz UHF. Chem. Commun. 2003, 2962

<A NAME="RZ25908SS-28F">28f</A> Li CC. Xie ZX. Zhang YD. Chen JH. Yang Z. J. Org. Chem. 2003, 68: 8500

<A NAME="RZ25908SS-28G">28g</A> Tsang KY. Brimble MA. Bremner JB. Org. Lett. 2003, 5: 4425

<A NAME="RZ25908SS-28H">28h</A> Paterson I. Davies RDM. Heimann AL. Maquez R. Meyer A. Org. Lett. 2003, 5: 4477

<A NAME="RZ25908SS-28I">28i</A> Lane JW. Halcomb RL. Org. Lett. 2003, 5: 4017

<A NAME="RZ25908SS-28J">28j</A> Hansen TM. Engler MM. Forsyth CJ. Bioorg. Med. Chem. Lett. 2003, 13: 2127

<A NAME="RZ25908SS-28K">28k</A> Ohyaba N. Nishkawa T. Isobe M. J. Am. Chem. Soc. 2003, 125: 8798

<A NAME="RZ25908SS-28L">28l</A> Marshall JA. Schaaf GM. J. Org. Chem. 2003, 68: 7428

<A NAME="RZ25908SS-28M">28m</A> Lopez S. Fernandeztrillo F. Castedo L. Saa C. Org. Lett. 2003, 5: 3275

<A NAME="RZ25908SS-29A">29a</A> Feuerstein M. Doucet H. Santelli M. Tetrahedron Lett. 2004, 45: 1603

<A NAME="RZ25908SS-29B">29b</A> Heuzé K. Méry D. Gauss D. Astruc D. Chem. Commun. 2003, 2274

<A NAME="RZ25908SS-29C">29c</A> Méry D. Heuzé K. Astruc D. Chem. Commun. 2003, 1934

<A NAME="RZ25908SS-29D">29d</A> Soheili A. Albaneze-Walker J. Murry JA. Dormer PG. Hughes DL. Org. Lett. 2003, 5: 4191

<A NAME="RZ25908SS-29E">29e</A> Mas-Marzá E. Segarra AM. Claver C. Peris E. Fernandez E. Tetrahedron Lett. 2003, 44: 6595

<A NAME="RZ25908SS-29F">29f</A> Leadbeater NE. Tominack BJ. Tetrahedron Lett. 2003, 44: 8653

<A NAME="RZ25908SS-30A">30a</A> Wang L. Li P. Zhang Y. Chem. Commun. 2004, 514

<A NAME="RZ25908SS-30B">30b</A> Beletskaya IP. Latyshev GV. Tsvetkov AV. Lukashev NV. Tetrahedron Lett. 2003, 44: 5011

<A NAME="RZ25908SS-31">31</A> Dams M. Drijkoningen L. Pauwels B. Van Tendeloo G. De Vos DE. Jacobs PA. J. Catal. 2002, 209: 225

<A NAME="RZ25908SS-32">32</A> Lee D.-H. Kim J.-H. Jun B.-H. Kang H. Park J. Lee Y.-S. Org. Lett. 2008, 10: 1609

<A NAME="RZ25908SS-33">33</A> Encyclopedia of Reagents for Organic Synthesis Vol. 4: John Wiley & Sons; Chichester: 1992. p.2301

<A NAME="RZ25908SS-34">34</A> France H. Heilbron IM. Hey DH. J. Chem. Soc. 1939, 1288

<A NAME="RZ25908SS-35">35</A> Dictionary of Organic Compounds Chapman and Hall; London: 1982. 5th ed.. p.5119

<A NAME="RZ25908SS-36">36</A> Dictionary of Organic Compounds Chapman and Hall; London: 1987. 5th ed., Suppl. 5. p.270

<A NAME="RZ25908SS-37">37</A> Modena G. Rivetti F. Tonellato U. J. Org. Chem. 1978, 43: 1521