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Synthesis 2011(7): 1125-1131
DOI: 10.1055/s-0030-1258452
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
Weitere Informationen
Received
3 December 2010
Publikationsdatum:
01. März 2011 (online)
Publikationsverlauf
Publikationsdatum:
01. März 2011 (online)
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
- 1
Heck RF. Acc. Chem. Res. 1979, 12: 146 -
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. -
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 -
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. -
3b
Whitcombe NJ.Hii KK.Gibson SE. Tetrahedron 2001, 57: 7449 -
4a
de Vries JG. Can. J. Chem. 2001, 79: 1086 -
4b
Blaser H.-U.Indolese A.Schnyder A.Steiner H.Studer M. J. Mol. Catal. A: Chem. 2001, 173: 3 -
4c
Tucker CE.de Vries JG. Top. Catal. 2002, 19: 111 -
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 -
5a
Littke AF.Fu GC. J. Org. Chem. 1999, 64: 10 -
5b
Littke AF.Fu GC. J. Am. Chem. Soc. 2001, 123: 6989 -
5c
Shaughnessy KH.Kim P.Hartwig JF. J. Am. Chem. Soc. 1999, 121: 2123 -
5d
Ehrentraut A.Zapf A.Beller M. Synlett 2000, 1589 -
5e
Bohm VPW.Herrmann WA. Chem. Eur. J. 2000, 6: 1017 -
6a
Herrmann WA.Brossmer C.Oefele K.Reisinger C.-P.Priermeier T.Beller M.Fischer H. Angew. Chem., Int. Ed. Engl. 1995, 34: 1844 -
6b
Herrmann WA.Brossmer C.Reisinger C.-P.Priermeier TH.Oefele K.Beller M. Chem. Eur. J. 1997, 3: 1357 -
6c
Ohff M.Ohff A.van der Boom ME.Milstein D. J. Am. Chem. Soc. 1997, 119: 11687 -
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 -
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 -
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 -
7e
Munoz MP.Martin-Matute B.Fernández-Rivas C.Cárdenas DJ.Echavarren AM. Adv. Synth. Catal. 2001, 343: 338 -
7f
Beletskaya IP.Kashin AN.Karlstedt NB.Mitin AV.Cheprakov AV.Kazankov GM. J. Organomet. Chem. 2001, 622: 89 -
7g
Alonso DA.Nájera C.Pacheco MC. Adv. Synth. Catal. 2002, 344: 172 -
7h
Rocaboy C.Gladysz JA. Org. Lett. 2002, 4: 1993 -
7i
Consorti CS.Zanini ML.Leal S.Ebeling G.Dupont J. Org. Lett. 2003, 5: 983 -
8a
Gruber AS.Zim D.Ebeling G.Monteriro AL.Dupont J. Org. Lett. 2000, 2: 1287 -
8b
Bergbreiter DE.Osburn PL.Wilson A.Sink E. J. Am. Chem. Soc. 2000, 122: 9058 -
9a
Bourissou D.Guerret O.Gabaï FP.Bertrand G. Chem. Rev. 2000, 100: 39 -
9b
Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290 - 10
Yang C.Lee HM.Nolan SP. Org. Lett. 2001, 3: 1511 - 11
Yao Q.Kinney EP.Yang Z. J. Org. Chem. 2003, 68: 7528 -
12a
Jeffery T. In Advances in Metal-Organic Chemistry Vol. 5:Liebeskind LS. JAI Press; Greenwich: 1996. p.153 -
12b
Bohm VPW.Herrmann WA. Chem. Eur. J. 2000, 6: 1017 -
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 -
12e
Kohler K.Heidenreich RG.Krauter JGE.Pietsch J. Chem. Eur. J. 2002, 8: 622 -
12f
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 -
12g
van der Boom ME.Milstein D. Chem. Rev. 2003, 103: 1759 -
12h
Bedford RB. Chem. Commun. 2003, 1787 -
12i
Beletskaya IP.Cheprakov AV. J. Organomet. Chem. 2004, 689: 4055 -
12j
Peris E.Crabtree RH. Coord. Chem. Rev. 2004, 248: 2239 -
12k
Christmann U.Vilar R. Angew. Chem. Int. Ed. 2005, 44: 366 -
13a
Reetz MT.Breinbauer R.Wanninger K. Tetrahedron Lett. 1996, 37: 4099 -
13b
Beller M.Fischer H.Kühlein K.Reisinger C.-P.Herrmann WA. J. Organomet. Chem. 1996, 520: 257 -
13c
Reetz MT.Westermann E. Angew. Chem. Int. Ed. 2000, 39: 165 -
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 -
14c
Eberhard MR. Org. Lett. 2004, 6: 2125 -
15a
Reetz MT.Westermann E. Angew. Chem. Int. Ed. 2000, 39: 165 -
15b
Sengupta S.Bhattacharyya S. Tetrahedron Lett. 1995, 36: 4475 -
15c
Crisp GT.Gebauer MG. Tetrahedron 1996, 52: 12465 -
15d
Desmazeau P.Legros J.-Y.Fiaud J.-C. Tetrahedron Lett. 1998, 39: 6707 -
15e
Reetz MT.Lohmer G.Schwickardi R. Angew. Chem. Int. Ed. 1998, 37: 481 -
15f
Reetz MT.Westermann E.Lohmer R.Lohmer G. Tetrahedron Lett. 1998, 39: 8449 -
15g
Bråthe A.Gundersen L.-L.Rise F.Eriksen AB.Vollsnes AV.Wang L. Tetrahedron 1999, 55: 211 -
15h
Carmichael AJ.Earle MJ.Holbrey JD.McCormac PB.Seddon KR. Org. Lett. 1999, 1: 997 -
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 -
15j
Okubo K.Shirai M.Yokoyama C. Tetrahedron Lett. 2002, 43: 7115 -
15k
Chandrasekhar S.Narsihmulu C.Sultana SS.Reddy NR. Org. Lett. 2002, 4: 4399 -
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 -
18b
Genet JP.Savignac M. J. Organomet. Chem. 1999, 576: 305 -
19a
Botella L.Nájera C. Tetrahedron Lett. 2004, 45: 1833 -
19b
Mukhopadhyay S.Rothenberg G.Joshi A.Baidossi M.Sasson Y. Adv. Synth. Catal. 2002, 344: 348 -
19c
Uozumi Y.Kimura T. Synlett 2002, 2045 - 20
Adam D. Nature 2003, 421: 571 -
21a
Gedye R.Smith F.Westaway K.Ali H.Baldisera L.Laberge L.Rousel R. Tetrahedron Lett. 1986, 27: 279 -
21b
Giguere RJ.Bary TL.Duncan SM.Majetich G. Tetrahedron Lett. 1986, 27: 4945 -
22a
Loupy A. Microwaves in Organic Synthesis 2nd ed.: Wiley-VCH; Weinheim: 2002. -
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 -
23b
Caddick S. Tetrahedron 1995, 51: 10403 -
23c
Galema SA. Chem. Soc. Rev. 1997, 26: 233 -
23d
Lidström P.Fierney J.Wathey B.Westman J. Tetrahedron 2001, 57: 9225 -
23e
Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250 -
23f
Hayes BL. Aldrichimica Acta 2004, 37: 66 -
23g
Roberts BA.Strauss CR. Acc. Chem. Res. 2005, 38: 653 -
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 -
25b
Razzaq T.Kappe CO. ChemSusChem 2008, 1: 123 -
25c
Varma RS. Green Chem. 2008, 10: 1129 -
26a
De la Hoz A.Díaz-Ortíz A.Moreno A. Curr. Org. Chem. 2004, 8: 903 -
26b
Langa F.De la Cruz P.De la Hoz A.Díaz-Ortíz A.Díez-Barra E. Contemp. Org. Synth. 1997, 4: 373 -
27a
Raghuvanshi DS.Singh KN. Synlett 2011, 373 -
27b
Raghuvanshi DS.Singh KN. ARKIVOC 2010, (x): 305 -
27c
Singh KN.Singh SK. ARKIVOC 2009, (xiii): 153 -
27d
Singh SK.Singh KN. J. Heterocycl. Chem. 2010, 47: 194 - 28
Pottabathula S.Keesara S.Likhar PR.Balsubramanian S.Kakita VM.Bhargava S.Mannepalli LK. J. Organomet. Chem. 2011, 696: 795 - 29
Yuan D.-Y.Tu Y.-Q.Fan C.-A. J. Org. Chem. 2008, 73: 7797 - 30
Modak A.Mondal J.Aswal VK.Bhaumik A. J. Mater. Chem. 2010, 20: 8099 - 31
Dong D.-J.Li H.-H.Tian S.-K. J. Am. Chem. Soc. 2010, 132: 5018 - 32
Denmark SE.Edwards MG. J. Org. Chem. 2006, 71: 7293