PEG-Supported Imidazolium Chloride: A Highly Efficient and Reusable Reaction Medium for the Heck Reaction

Liang Wang; Yuhong Zhang; Chunsong Xie; Yanguang Wang

doi:10.1055/s-2005-871566

LETTER

PEG-Supported Imidazolium Chloride: A Highly Efficient and Reusable Reaction Medium for the Heck Reaction

Liang Wang, Yuhong Zhang*, Chunsong Xie, Yanguang Wang*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
e-Mail: yhzhang@zjuem.zju.edu.cn; e-Mail: orgwyg@zju.edu.cn;

Abstract

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Abstract

Pd(OAc)₂ in [PEGmim][Cl] constituted a highly efficient and recyclable catalytic system for the Heck reaction of aryl bromides and activated aryl chlorides in the absence of ligands.

Key words

Heck reaction - ionic liquids - PEG

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References

1a Bräse S. Meijere A. In Metal-Catalyzed Cross-Coupling Reactions Diederich F., Stang P. J., Wiley-VCH; Weinheim: 1998. p.99-166

1b Beletskaya IP. Cheprakov AV. Chem. Rev. 2000, 100: 3009

1c Dounay AB. Overman LE. Chem. Rev. 2003, 103: 2945

2a Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176

2b Cornils B. Herrmann WA. Applied Homogeneous Catalysis with Organometallic Compounds VCH; Weinheim: 1996.

2c Beller M. Bolm C. Transition Metals for Organic Synthesis Wiley-VCH; Weinheim: 1998.

3a Zhao F. Bhanage BM. Shirai M. Arai M. Chem.-Eur. J. 2000, 6: 843

3b Bhanage BM. Shirai M. Arai M. J. Mol. Catal. A: Chem. 1999, 145: 69

3c Varma RS. Naicker KP. Leisen PJ. Tetrahedron Lett. 1999, 40: 2075

3d Biffis A. Zecca M. Basato M. Eur. J. Inorg. Chem. 2001, 1131

3e Djakovitch L. Koehler K. J. Am. Chem. Soc. 2001, 123: 5990

3f Djakovitch L. Koehler K. J. Mol. Catal. A: Chem. 1999, 142: 275

3g Biffis A. Zecca M. Basato M. J. Mol. Catal. A: Chem. 2001, 173: 249

3h Augustine RL. Buchmeiser MR. Schareina T. Kempe R. Wurst K. J. Organomet. Chem. 2001, 634: 39

3i Li J. Mau AW.-H. Strauss CR. Chem. Commun. 1997, 1275

3j Tonks L. Anson MS. Hellgardt K. Mirza AR. Thompson DF. Williams JMJ. Tetrahedron Lett. 1997, 38: 4319

4a Reetz MT. de Vries JG. Chem. Commun. 2004, 1559

4b Klingelhofer S. Heitz W. Greiner A. Oestreich S. Forster S. Antonietti M. J. Am. Chem. Soc. 1997, 119: 10116

4c Li Y. Hong XM. Collard DM. El-Sayed MA. Org. Lett. 2000, 2: 2385

4d Pham-Huu C. Keller N. Charbonniere LJ. Ziessel R. Ledoux MJ. Chem. Commun. 2000, 1871

4e Choudary BM. Chowdari NS. Jyothi K. Kumar NS. Kantam ML. Chem. Commun. 2002, 586

4f Kiraly Z. Veisz B. Mastalir A. Razga Z. Dekany I. Chem. Commun. 1999, 1925

4g Reetz MT. Westermann E. Angew Chem. Int. Ed. 2000, 39: 165

5a Gruber AS. Zim D. Ebeling G. Monteiro AL. Dupont J. Org. Lett. 2000, 2: 1287

5b Bergbreiter DE. Osburn PL. Wilson A. Sink EM. J. Am. Chem. Soc. 2000, 122: 9058

5c Gruber AS. Pozebon D. Monteiro L. Dupont J. Tetrahedron Lett. 2001, 42: 7345

6a Consorti CS. Zanini ML. Leal S. Ebeling G. Dupont J. Org. Lett. 2003, 5: 983

6b Beletskaya IP. Kashin AN. Karlstedt NB. Mitin AV. Cheprakov AV. Kazankov GM. J. Organomet. Chem. 2001, 622: 89

6c Yao Q. Kinney EP. Yang Z. J. Org. Chem. 2003, 68: 7528

6d Rocaboy C. Gladysz JA. Org. Lett. 2002, 4: 1993

7a Bourissou D. Guerret O. Gabba FP. Bertrand CB. Chem. Rev. 2000, 100: 39

7b Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290

7c Nolan SP. Lee HM. Yang C. Org. Lett. 2001, 3: 1511

7d Regitz M. Angew. Chem., Int. Ed. Engl. 1996, 35: 725

8a Hussey CL. Quigley R. Seddon KR. Inorg. Chem. 1995, 34: 370

8b Welton T. Chem. Rev. 1999, 99: 2071

8c Wasserscheid P. Keim W. Angew. Chem. Int. Ed. 2000, 39: 3773

8d Dupont J. de Souza RF. Suarez PAZ. Chem. Rev. 2002, 102: 3667

9a Jeffery T. Tetrahedron 1996, 52: 10113

9b Kaufmann DE. Nouroozian M. Henze H. Synlett 1996, 1091

9c Calo V. Nacci A. Monopoli A. Lopez L. Cosmo A. Tetrahedron 2001, 57: 6071

9d Silberg J. Schareina T. Kempe R. Wurst K. Buchmeiser MR. J. Organomet. Chem. 2001, 622: 6

9e Boehm VPW. Gstoettmayr CWK. Weskamp T. Herrmann WA. J. Organomet. Chem. 2000, 595: 186

9f Bouquillon S. Ganchegui B. Estrine B. Henin F. Muzart J. J. Organomet. Chem. 2001, 634: 153

9g Choudary BM. Madhi S. Chowdari NS. Kantam ML. Sreedhar B. J. Am. Chem. Soc. 2002, 124: 14127

9h Park SB. Alper H. Org. Lett. 2003, 5: 3209

9i Xiao JC. Twamley B. Shreeve JM. Org. Lett. 2004, 6: 3845

9j Hagiwara H. Sugawara Y. Isobe K. Hoshi T. Suzuki T. Org. Lett. 2004, 6: 2325

9k Liu SF. Fukuyama T. Sato M. Ryu I. Synlett 2004, 1814

10 Boehm VP. Herrmann WA. Chem.-Eur. J. 2000, 6: 1017

11a Mehnert CP. Cook RA. Dispenziere NC. Afeworki M. J. Am. Chem. Soc. 2002, 124: 12932

11b Kim DW. Chi DY. Angew. Chem. Int. Ed. 2004, 43: 483

11c Mehnert CP. Mozeleski EJ. Cook RA. Chem. Commun. 2002, 3010

11d Handy ST. Okello M. Dickenson G. Org. Lett. 2003, 5: 2513

12a Heldebrant DJ. Jessop PG. J. Am. Chem. Soc. 2003, 125: 5600

12b Chandrasekhar S. Narsihmulu C. Sultana SS. Reddy NR. Chem. Commun. 2003, 1716

13a Chandrasekhar S. Narsihmulu Ch. Sultana SS. Reddy NR. Org. Lett. 2002, 4: 4399

13b Luo C. Zhang Y. Wang Y. J. Mol. Catal. A: Chem. 2005, 229: 7

14 Lin XF. Zhang J. Cui SL. Wang YG. Synthesis 2003, 1569

15 Schwarz J. Boehm VPW. Gardiner MG. Grosche M. Herrmann WA. Hieringer W. Raudaschl-Sieber G. Chem.-Eur. J. 2000, 6: 1773

16a Zhang C. Huang J. Trudell ML. Nolan SP. J. Org. Chem. 1999, 64: 3804

16b Lee HM. Nolan SP. Org. Lett. 2000, 2: 2053

16c Herrmann WA. Boehm VPW. J. Organomet. Chem. 1999, 572: 141

16d Huang J. Grasa G. Nolan SP. Org. Lett. 1999, 1: 1307

16e Carmichael AJ. Earle MJ. Holbrey JD. McCormac PB. Seddon KR. Org. Lett. 1999, 1: 997

16f Xu L. Chen W. Xiao J. Organometallics 2000, 19: 1123

16g Yang C. Nolan SP. Synlett 2001, 1539