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Synthesis 2010(14): 2399-2406
DOI: 10.1055/s-0029-1218776
DOI: 10.1055/s-0029-1218776
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Suzuki and Sonogashira Cross-Coupling Reactions in Water Medium with a Reusable Poly(N-vinylcarbazole)-Anchored Palladium(II) Complex
Further Information
Received
1 February 2010
Publication Date:
05 May 2010 (online)
Publication History
Publication Date:
05 May 2010 (online)
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Abstract
Poly(3,6-dibenzaldimino-N-vinylcarbazole)-anchored palladium(II) complex has been synthesized and characterized by different physicochemical and spectroscopic techniques. The present complex shows excellent catalytic activities for Suzuki and Sonogashira coupling reactions under phosphine-free and copper-free reaction conditions in water medium. This immobilized catalyst can be easily separated and reused for further reactions for more than five times without noticeable loss in the catalytic activity.
Key words
heterogeneous catalysis - Schiff base - palladium complex - cross-coupling - biaryls
-
1a
Stetter J.Lieb F. Angew. Chem. Int. Ed. 2000, 39: 1724 -
1b
Negishi E.Anastasia L. Chem. Rev. 2003, 103: 1979 -
1c
Nicolaou KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4442 -
2a
Chinchilla R.Nájera C. Chem. Rev. 2007, 107: 874 -
2b
Nicolaou KC.Boddy CNC.Brase S.Winssinger N. Angew. Chem. Int. Ed. 1999, 38: 2096 -
2c
Baudoin O.Cesario M.Guenard D.Gueritte F. J. Org. Chem. 2002, 67: 1199 -
2d
Tsuji J. Palladium Reagents and Catalysts Wiley; New York: 1995. -
2e
Paterson I.Davies RDM.Marquez R. Angew. Chem. Int. Ed. 2001, 40: 603 -
2f
Mongin O.Porres L.Moreaux L.Mertz J.Blanchard-Desce M. Org. Lett. 2002, 4: 719 -
3a
Shaughnessy KH. Eur. J. Org. Chem. 2006, 1827 -
3b
Li CJ. Chem. Rev. 1993, 93: 2023 -
3c
Li CJ. Chem. Rev. 2005, 105: 3095 -
3d
Guan JT.Weng TQ.Yu G.Liu SH. Tetrahedron Lett. 2007, 48: 7129 -
3e
Wan Y.Wang H.Zhao Q.Klingstedt M.Terasaki O.Zhao D. J. Am. Chem. Soc. 2009, 131: 4541 -
4a
Zhao FY.Bhanage BM.Shirai M.Arai M. J. Mol. Catal. A: Chem. 1999, 142: 383 -
4b
Reetz MT.de Vries JG. Chem. Commun. 2004, 1559 -
4c
Komáromi A.Tolnai GL.Novák Z. Tetrahedron Lett. 2008, 49: 7294 -
4d
Bakherad M.Keivanloo A.Bahramian B.Hashemi M. Tetrahedron Lett. 2009, 50: 1557 -
5a
Mora M.Jiménez-Sanchidrián C.Ruiz JR. J. Mol. Catal. A: Chem. 2008, 285: 79 -
5b
Shimizu K.Maruyama R.Komai S.Kodama T.Kitayama Y. J. Catal. 2004, 227: 202 -
5c
Reddy EA.Barange DK.Islam A.Mukkanti V.Pal M. Tetrahedron. 2008, 64: 7143 -
5d
Jana S.Dutta B.Bera R.Koner S. Inorg. Chem. 2008, 47: 5512 -
5e
Crudden CM.Sateesh M.Lewis R. J. Am. Chem. Soc. 2005, 127: 10045 -
5f
Kang C.Huang J.He W.Zhang F. J. Organomet. Chem. 2010, 695: 120 -
5g
Mayr M.Mayr B.Buchmeiser MR. Angew. Chem. Int. Ed. 2001, 40: 3839 -
5h
Byun JW.Lee YS. Tetrahedron Lett. 2004, 45: 1837 -
5i
Kim JH.Jun BH.Byun JW.Lee YS. Tetrahedron Lett. 2004, 45: 5827 -
6a
Kim JW.Kim JH.Lee D.Lee Y. Tetrahedron Lett. 2006, 47: 4745 -
6b
Uozumi Y. Top. Curr. Chem. 2004, 242: 77 -
6c
Guino M.Hii KKM. Chem. Soc. Rev. 2007, 36: 608 -
7a
Wang S.Zhang Z.Hu Z.Wang Y.Lei P.Chi H. J. Environ. Sci. 2009, 21: S124 -
7b
Pelagatti P.Carcelli M.Costa M.Ianelli S.Pelizzi C.Rogolino D. J. Mol. Catal. A: Chem. 2005, 226: 107 -
7c
Kang YK.Kim DY. Tetrahedron Lett. 2006, 27: 4565 -
8a
Cai M.Sha J.Xu Q. J. Mol. Catal. A: Chem. 2007, 268: 82 -
8b
Wolf C.Lerebours R. Org. Biomol. Chem. 2004, 2: 2161 -
8c
Zhao H.Wang Y.Sha J.Sheng S.Cai M. Tetrahedron 2008, 64: 7517 -
8d
Uozumi Y.Danjo H.Hayashi T. Tetrahedron Lett. 1998, 39: 8303 -
8e
Uozumi Y.Danjo H.Hayashi T. J. Org. Chem. 1999, 64: 3384 -
8f
Uozumi Y.Nakai Y. Org. Lett. 2002, 4: 2997 -
8g
Uozumi Y.Kikuchi M. Synlett 2005, 1775 -
9a
Phan NTS.Styring P. Green Chem. 2008, 10: 1055 -
9b
Mohanty S.Suresh D.Balakrishna MS.Mague JT. J. Organomet. Chem. 2009, 694: 2114 - 10
King RB.Sweet EM. J. Org. Chem. 1979, 44: 385 - 11
Kharasch MS.Seyler RC.Mayo FR. J. Am. Chem. Soc. 1983, 60: 822 - 12
Onue H.Moritani I. J. Organomet. Chem. 1972, 43: 431 - 13
Durig JR.Layton R.Sink DW.Mitchell BR. Spectrochim. Acta 1965, 21: 1367 - 14
Santra PK.Sagar P. J. Mol. Catal. A: Chem. 2003, 197: 37 -
15a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
15b
Suzuki A. J. Organomet. Chem. 1999, 576: 147 -
15c
Suzuki A. J. Organomet. Chem. 2002, 653: 83 -
15d
Miyaura N. Top. Curr. Chem. 2002, 11 -
15e
Miyaura N. Metal-Catalyzed Cross-Coupling Reactions 2nd ed., Vol. 1:de Meijere A.Diederich F. Wiley-VCH; Weinheim: 2004. p.41-124 -
16a
Sonogashira K. J. Organomet. Chem. 2002, 653: 46 -
16b
Negishi E.Anastasia L. Chem. Rev. 2003, 103: 1979 -
17a
Sin E.Yi S.Lee Y. J. Mol. Catal. A: Chem. 2010, 315: 99 -
17b
Wang L.Cai C. J. Mol. Catal. A: Chem. 2009, 306: 97 -
17c
Bandini M.Luque R.Budarin V.Macquarrie DJ. Tetrahedron 2005, 61: 9860 -
17d
Bakherad M.Keivanloo A.Bahramian B.Hashemi M. Tetrahedron Lett. 2009, 50: 1557 -
17e
Liang B.Dai M.Chen J.Yang Z. J. Org. Chem. 2005, 70: 391