Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(4): 692-698
DOI: 10.1055/s-2006-926305
DOI: 10.1055/s-2006-926305
PAPER
© Georg Thieme Verlag Stuttgart · New York
Palladium on Activated Carbon - A Recyclable Catalyst for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides in Water
Further Information
Received
24 August 2005
Publication Date:
19 January 2006 (online)
Publication History
Publication Date:
19 January 2006 (online)
Abstract
Aryl chlorides are efficiently coupled with aryl boronic acids using ligandless Pd/C in water. The catalyst is easily recovered via filtration and reused up to four times with an overall yield of 73%. In addition the catalytic activity and selectivity of a variety of homogeneous and heterogeneous palladium sources have been compared.
Key words
aryl chlorides - water - palladium - cross-coupling - biaryls
-
1a
Miyaura N.Yanagi T.Suzuki A. Synth. Commun. 1981, 11: 513 -
1b
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
1c
Suzuki A. J. Organomet. Chem. 1999, 576: 147 -
2a
Stanford SP. Tetrahedron 1998, 54: 263 -
2b
Smith GB.Dezeny GC.Hughes DL.King AO.Verthoeven TR. J. Org. Chem. 1994, 59: 8151 -
3a For a recent review, see:
Bellina F.Carpita A.Rozzi R. Synthesis 2004, 2419 -
3b See also:
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 - 4
Shaughnessy KH.DeVasher RB. Curr. Org. Chem. 2005, 9: 585 -
5a
Badone D.Baroni R.Cardamone A.Ielmini A.Guzzi U. J. Org. Chem. 1997, 62: 7170 -
5b
Arcadi A.Cerichelli G.Chiarini M.Correa M.Zorzan D. Eur. J. Org. Chem. 2003, 4080 -
5c
Lu G.Franzén R.Zhang Q.Xu Y. Tetrahedron Lett. 2005, 46: 4255 -
5d
Arvela RK.Leadbeater NE.Sangi MS.Williams VA.Granados P.Singer R. J. Org. Chem. 2005, 70: 161 -
6a
Arvela KR.Leadbeater NE. Org. Lett. 2005, 7: 2101 -
6b
Bumagin NA.Bykov VV. Tetrahedron 1997, 53: 14437 -
6c
Bedford RB.Blake ME.Butts CP.Holder D. Chem. Commun. 2003, 466 - 7
Lysén M.Köhler K. Synlett 2005, 1671 -
8a
Heidenreich RG.Krauter JGE.Pietsch J.Köhler K. J. Mol. Catal. A: Chem. 2002, 182-183: 499 -
8b
Biffis A.Zecca M.Basato M. J. Mol. Catal. A: Chem. 2001, 173: 249 - 9
Heidenreich RG.Köhler K.Krauter JGE.Pietsch J. Synlett 2002, 1118 - 10
Reetz MT.de Vries JG. Chem. Commun. 2004, 1559 - 11
Wright W.Hageman DL.McClure LD. J. Org. Chem. 1994, 59: 6095 - 12
Tagata T.Nishida M. J. Org. Chem. 2003, 68: 9412 -
13a
Chaumeil H.Signorella S.Drian CL. Tetrahedron 2000, 56: 9655 -
13b
Kristensen JL.Lysén M.Vedsø P.Begtrup M. Org. Lett. 2001, 3: 1435 -
13c
Barder TE.Walker SD.Martinelli JR.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4685 -
14a
Vedejs J.Chapman RW.Fields SC.Lin S.Schrimpf MR. J. Org. Chem. 1995, 60: 3020 -
14b
Molander GA.Biolatto B. Org. Lett. 2002, 4: 1867 -
14c
Barder TE.Buchwald SL. Org. Lett. 2004, 6: 2649 - 15
Pröckl SS.Kleist W.Gruber MA.Köhler K. Angew. Chem. Int. Ed. 2004, 43: 1881 - 16
de Vries AHM.Parlevliet FJ.Vondervoort LS.Mommers JHM.Henderickx HJW.Walet MAM.de Vries JG. Adv. Synth. Catal. 2002, 344: 996 - 17
Wolfe JP.Singer RA.Yang BH.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9550 - 18
Leadbeater N. J. Org. Chem. 2001, 66: 7539 - 19
Zapf A.Beller M. Chem. Eur. J. 2000, 6: 1830 - 20
Riggleman S.DeShong P. J. Org. Chem. 2003, 68: 8106 - 21
Glover SA.Goosen A.McCleland CW.Schoonraad JL. J. Chem. Soc., Perkin Trans. 1 1984, 10: 2255 - 22
Old DW.Wolfe JP.Buchwald SL. J. Am. Chem. Soc. 1998, 120: 9722 - 23
Kabalka GW.Wang L.Pagni RM.Hair MC.Namboodiri V. Synthesis 2003, 217 - 24
Nájera C.Gil-Molto J.Karlström S.Falvello LR. Org. Lett. 2003, 5: 1451 - 25
Herndon JW.McMullen LA. J. Organomet. Chem. 1989, 368: 83 - 26
Li J.-L.Liu N.-J. Org. Lett. 2004, 6: 2809 - 27
Downie IM.Hearey H.Kemp G.King D.Wosley M. Tetrahedron 1992, 48: 4005 - 28
Hermann EC.Hoyer G.-A.Kelm J. Spectrochim. Acta, Part A 1982, 38: 1057 - 29
Enokido T.Fugami K.Endo M.Kameyama M.Kosugi M. Adv. Synth. Catal. 2004, 346: 1685 - 30
Denmark SE.Ober MH. Org. Lett. 2003, 5: 1357