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

doi:10.1055/s-0030-1258452

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Synthesis 2011(7): 1125-1131
DOI: 10.1055/s-0030-1258452

PAPER

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)

Abstract
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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

Crossref Google Scholar
2a Heck RF. Palladium Reagents in Organic Synthesis Academic Press; London: 1985.

Google Scholar
2b Heck RF. In Comprehensive Organic Synthesis Vol 4: Trost BM. Fleming I. Pergamon; New York: 1991. Chap. 4.3.

Google Scholar
2c Negishi E.-I. Handbook of Organopalladium Chemistry for Organic Synthesis Wiley; New York: 2002.

Google Scholar
2d Tsuji J. Palladium Reagents and Catalysts Wiley; Chichester: 1995.

Google Scholar
2e The Mizoroki-Heck Reaction Oestreich M. Wiley; Chichester: 2009.

Google Scholar
2f Alonso F. Beletskaya IP. Yus M. Tetrahedron 2005, 61: 11771

Google Scholar
2g Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 2337

Google Scholar
3a de Meijere A. Diederich F. Metal-Catalyzed Cross-Coupling Reactions 2nd ed.: Wiley-VCH; Weinheim: 2004.

Google Scholar
3b Whitcombe NJ. Hii KK. Gibson SE. Tetrahedron 2001, 57: 7449

Google Scholar
4a de Vries JG. Can. J. Chem. 2001, 79: 1086

Google Scholar
4b Blaser H.-U. Indolese A. Schnyder A. Steiner H. Studer M. J. Mol. Catal. A: Chem. 2001, 173: 3

Google Scholar
4c Tucker CE. de Vries JG. Top. Catal. 2002, 19: 111

Google Scholar
4d de Vries JG. de Vries AHM. Eur. J. Org. Chem. 2003, 799

Google Scholar
4e Blaser H.-U. Indolese A. Naud F. Nettekoven U. Schnyder A. Adv. Synth. Catal. 2004, 346: 1583

Google Scholar
5a Littke AF. Fu GC. J. Org. Chem. 1999, 64: 10

Google Scholar
5b Littke AF. Fu GC. J. Am. Chem. Soc. 2001, 123: 6989

Google Scholar
5c Shaughnessy KH. Kim P. Hartwig JF. J. Am. Chem. Soc. 1999, 121: 2123

Google Scholar
5d Ehrentraut A. Zapf A. Beller M. Synlett 2000, 1589

Google Scholar
5e Bohm VPW. Herrmann WA. Chem. Eur. J. 2000, 6: 1017

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

Google Scholar
6b Herrmann WA. Brossmer C. Reisinger C.-P. Priermeier TH. Oefele K. Beller M. Chem. Eur. J. 1997, 3: 1357

Google Scholar
6c Ohff M. Ohff A. van der Boom ME. Milstein D. J. Am. Chem. Soc. 1997, 119: 11687

Google Scholar
6d Shaw BL. Perera SD. Staley EA. Chem. Commun. 1998, 1361

Google Scholar
6e Albisson DA. Bedford RB. Scully PN. Lawrence SE. Chem. Commun. 1998, 2095

Google Scholar
6f Miyazaki F. Yamaguchi K. Shibasaki M. Tetrahedron Lett. 1998, 39: 7379

Google Scholar
6g Morales-Morales D. Redón R. Yung C. Jensen CM. Chem. Commun. 2000, 1619

Google Scholar
6h Bedford RB. Welch SL. Chem. Commun. 2001, 129

Google Scholar
6i Gibson S. Foster DF. Eastam GR. Tooze RP. Cole-Hamilton DJ. Chem. Commun. 2001, 779

Google Scholar
7a Ohff M. Ohff A. Milstein D. Chem. Commun. 1999, 357

Google Scholar
7b Iyer S. Ramesh C. Tetrahedron Lett. 2000, 41: 8981

Google Scholar
7c Gai X. Grigg R. Ramzan MI. Sridharan V. Collard S. Muir JE. Chem. Commun. 2000, 2053

Google Scholar
7d Alonso DA. Nájera C. Pacheco MC. Org. Lett. 2000, 2: 1823

Google Scholar
7e Munoz MP. Martin-Matute B. Fernández-Rivas C. Cárdenas DJ. Echavarren AM. Adv. Synth. Catal. 2001, 343: 338

Google Scholar
7f Beletskaya IP. Kashin AN. Karlstedt NB. Mitin AV. Cheprakov AV. Kazankov GM. J. Organomet. Chem. 2001, 622: 89

Google Scholar
7g Alonso DA. Nájera C. Pacheco MC. Adv. Synth. Catal. 2002, 344: 172

Google Scholar
7h Rocaboy C. Gladysz JA. Org. Lett. 2002, 4: 1993

Google Scholar
7i Consorti CS. Zanini ML. Leal S. Ebeling G. Dupont J. Org. Lett. 2003, 5: 983

Google Scholar
8a Gruber AS. Zim D. Ebeling G. Monteriro AL. Dupont J. Org. Lett. 2000, 2: 1287

Google Scholar
8b Bergbreiter DE. Osburn PL. Wilson A. Sink E. J. Am. Chem. Soc. 2000, 122: 9058

Google Scholar
9a Bourissou D. Guerret O. Gabaï FP. Bertrand G. Chem. Rev. 2000, 100: 39

Google Scholar
9b Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290

Google Scholar
10 Yang C. Lee HM. Nolan SP. Org. Lett. 2001, 3: 1511

Crossref PubMed Google Scholar
11 Yao Q. Kinney EP. Yang Z. J. Org. Chem. 2003, 68: 7528

Crossref Google Scholar
12a Jeffery T. In Advances in Metal-Organic Chemistry Vol. 5: Liebeskind LS. JAI Press; Greenwich: 1996. p.153

Google Scholar
12b Bohm VPW. Herrmann WA. Chem. Eur. J. 2000, 6: 1017

Google Scholar
12c Dupont J. Pfeffer M. Spencer J. Eur. J. Inorg. Chem. 2001, 1917

Google Scholar
12d Biffis A. Zecca M. Basato M. J. Mol. Catal. A: Chem. 2001, 173: 249

Google Scholar
12e Kohler K. Heidenreich RG. Krauter JGE. Pietsch J. Chem. Eur. J. 2002, 8: 622

Google Scholar
12f Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176

Google Scholar
12g van der Boom ME. Milstein D. Chem. Rev. 2003, 103: 1759

Google Scholar
12h Bedford RB. Chem. Commun. 2003, 1787

Google Scholar
12i Beletskaya IP. Cheprakov AV. J. Organomet. Chem. 2004, 689: 4055

Google Scholar
12j Peris E. Crabtree RH. Coord. Chem. Rev. 2004, 248: 2239

Google Scholar
12k Christmann U. Vilar R. Angew. Chem. Int. Ed. 2005, 44: 366

Google Scholar
13a Reetz MT. Breinbauer R. Wanninger K. Tetrahedron Lett. 1996, 37: 4099

Google Scholar
13b Beller M. Fischer H. Kühlein K. Reisinger C.-P. Herrmann WA. J. Organomet. Chem. 1996, 520: 257

Google Scholar
13c Reetz MT. Westermann E. Angew. Chem. Int. Ed. 2000, 39: 165

Google Scholar
13d Reetz MT. de Vries JG. Chem. Commun. 2004, 1559

Google Scholar
14a Deshmukh RR. Rajagopal R. Srinivasan KV. Chem. Commun. 2001, 1544

Google Scholar
14b de Vries AHM. Mulders JMCA. Mommers JHM. Henderickx HJW. de Vries JG. Org. Lett. 2003, 5: 3285

Google Scholar
14c Eberhard MR. Org. Lett. 2004, 6: 2125

Google Scholar
15a Reetz MT. Westermann E. Angew. Chem. Int. Ed. 2000, 39: 165

Google Scholar
15b Sengupta S. Bhattacharyya S. Tetrahedron Lett. 1995, 36: 4475

Google Scholar
15c Crisp GT. Gebauer MG. Tetrahedron 1996, 52: 12465

Google Scholar
15d Desmazeau P. Legros J.-Y. Fiaud J.-C. Tetrahedron Lett. 1998, 39: 6707

Google Scholar
15e Reetz MT. Lohmer G. Schwickardi R. Angew. Chem. Int. Ed. 1998, 37: 481

Google Scholar
15f Reetz MT. Westermann E. Lohmer R. Lohmer G. Tetrahedron Lett. 1998, 39: 8449

Google Scholar
15g Bråthe A. Gundersen L.-L. Rise F. Eriksen AB. Vollsnes AV. Wang L. Tetrahedron 1999, 55: 211

Google Scholar
15h Carmichael AJ. Earle MJ. Holbrey JD. McCormac PB. Seddon KR. Org. Lett. 1999, 1: 997

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

Google Scholar
15j Okubo K. Shirai M. Yokoyama C. Tetrahedron Lett. 2002, 43: 7115

Google Scholar
15k Chandrasekhar S. Narsihmulu C. Sultana SS. Reddy NR. Org. Lett. 2002, 4: 4399

Google Scholar
16a Li C.-H. Chan T.-H. Organic Reactions in Aqueous Media John Wiley & Sons; New York: 1997.

Google Scholar
16b Cornils B. Herrmann WA. Aqueous Phase Organometallic Chemistry: Concepts and Applications Wiley-VCH; Weinheim: 1998.

Google Scholar
16c Organic Synthesis in Water Grieco PA. Blackie Academic & Professional; London: 1998.

Google Scholar
16d Joo F. Aqueous Organometallic Catalysis Kluwer; Dordrecht: 2001.

Google Scholar
17a Metal Catalysis in Water Grieco PA. Blackie Academic & Professional; London: 1998.

Google Scholar
18a Sinou D. Top. Curr. Chem. 1999, 206: 41

Google Scholar
18b Genet JP. Savignac M. J. Organomet. Chem. 1999, 576: 305

Google Scholar
19a Botella L. Nájera C. Tetrahedron Lett. 2004, 45: 1833

Google Scholar
19b Mukhopadhyay S. Rothenberg G. Joshi A. Baidossi M. Sasson Y. Adv. Synth. Catal. 2002, 344: 348

Google Scholar
19c Uozumi Y. Kimura T. Synlett 2002, 2045

Google Scholar
20 Adam D. Nature 2003, 421: 571

Crossref Google Scholar
21a Gedye R. Smith F. Westaway K. Ali H. Baldisera L. Laberge L. Rousel R. Tetrahedron Lett. 1986, 27: 279

Google Scholar
21b Giguere RJ. Bary TL. Duncan SM. Majetich G. Tetrahedron Lett. 1986, 27: 4945

Google Scholar
22a Loupy A. Microwaves in Organic Synthesis 2nd ed.: Wiley-VCH; Weinheim: 2002.

Google Scholar
22b Hayes BL. Microwave Synthesis: Chemistry at the Speed of Light CEM Publishing; Matthews (NC): 2002.

Google Scholar
22c Lidstrom P. Tierney JP. Microwave-Assisted Organic Synthesis Blackwell Scientific; Oxford: 2005.

Google Scholar
22d Kappe CO. Stadler A. Microwaves in Organic and Medicinal Chemistry Wiley-VCH; Weinheim: 2005.

Google Scholar
22e Kappe CO. Dallinger DS. Murphree S. Practical Microwave Synthesis for Organic Chemists: Strategies, Instruments, and Protocols Wiley-VCH; Weinheim: 2009.

Google Scholar
23a Bose AK. Manhas MS. Banik BK. Robb EW. Res. Chem. Intermed. 1994, 20: 1

Google Scholar
23b Caddick S. Tetrahedron 1995, 51: 10403

Google Scholar
23c Galema SA. Chem. Soc. Rev. 1997, 26: 233

Google Scholar
23d Lidström P. Fierney J. Wathey B. Westman J. Tetrahedron 2001, 57: 9225

Google Scholar
23e Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250

Google Scholar
23f Hayes BL. Aldrichimica Acta 2004, 37: 66

Google Scholar
23g Roberts BA. Strauss CR. Acc. Chem. Res. 2005, 38: 653

Google Scholar
24a Anastas PT. Warner JC. Green Chemistry: Theory and Practice Oxford University Press; New York: 2000.

Google Scholar
24b Anastas PT. Williamson TC. Green Chemistry: Frontiers in Benign Chemical Synthesis and Process Oxford University Press; New York: 1998.

Google Scholar
25a Dallinger D. Kappe CO. Chem. Rev. 2007, 107: 2563

Google Scholar
25b Razzaq T. Kappe CO. ChemSusChem 2008, 1: 123

Google Scholar
25c Varma RS. Green Chem. 2008, 10: 1129

Google Scholar
26a De la Hoz A. Díaz-Ortíz A. Moreno A. Curr. Org. Chem. 2004, 8: 903

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

Google Scholar
27a Raghuvanshi DS. Singh KN. Synlett 2011, 373

Google Scholar
27b Raghuvanshi DS. Singh KN. ARKIVOC 2010, (x): 305

Google Scholar
27c Singh KN. Singh SK. ARKIVOC 2009, (xiii): 153

Google Scholar
27d Singh SK. Singh KN. J. Heterocycl. Chem. 2010, 47: 194

Google Scholar
28 Pottabathula S. Keesara S. Likhar PR. Balsubramanian S. Kakita VM. Bhargava S. Mannepalli LK. J. Organomet. Chem. 2011, 696: 795

Crossref Google Scholar
29 Yuan D.-Y. Tu Y.-Q. Fan C.-A. J. Org. Chem. 2008, 73: 7797

Crossref Google Scholar
30 Modak A. Mondal J. Aswal VK. Bhaumik A. J. Mater. Chem. 2010, 20: 8099

Crossref Google Scholar
31 Dong D.-J. Li H.-H. Tian S.-K. J. Am. Chem. Soc. 2010, 132: 5018

Crossref Google Scholar
32 Denmark SE. Edwards MG. J. Org. Chem. 2006, 71: 7293

Crossref Google Scholar