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Synlett 2005(7): 1101-1104
DOI: 10.1055/s-2005-865198
DOI: 10.1055/s-2005-865198
LETTER
© Georg Thieme Verlag Stuttgart · New York
Copper-Catalyzed Etherification of Aryl Iodides Using KF/Al2O3: An Improved Protocol
Weitere Informationen
Received
24 September 2004
Publikationsdatum:
14. April 2005 (online)
Publikationsverlauf
Publikationsdatum:
14. April 2005 (online)
Abstract
A simple and efficient method for the coupling of aryl iodides with aliphatic alcohols and phenols that does not require the use of alkoxide bases is described. This C-O bond forming procedure shows that the combination of air stable CuI and 1,10-phenanthroline in the presence of KF/Al2O3 comprises an extremely efficient and general catalyst system for the etherification of aryl iodides. Different functionalized aryl iodides were coupled with alcohols and phenols using this method.
Key words
etherification - aryl iodides - copper iodide - potassium fluoride on alumina - coupling reaction
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1a
Simon J.Salzbrunn S.Suryaprakash GK.Petasis NA.Olah GA. J. Org. Chem. 2001, 66: 633 -
1b
Mann G.Hartwig JF. Tetrahedron Lett. 1997, 38: 8005 -
1c
Evans DA.Katz JL.West TR. Tetrahedron Lett. 1998, 39: 2937 -
1d
Pulley SHR.Ratasen S.Vorogushin A.Swanson E. Org. Lett. 1999, 1: 1721 -
1e
Nicolaou KC.Boddy CNC.Natarajan S.Yue TY.Li H.Brase S.Ramanjulu JM. J. Am. Chem. Soc. 1997, 119: 3421 -
1f
Palucki M.Wolfe JP.Buchwald SL. J. Am. Chem. Soc. 1997, 119: 3395 -
2a
Ley SV.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400 -
2b
Ma D.Cai Q. Org. Lett. 2003, 5: 3799 -
2c
Wolter M.Nordmann G.Job GE.Buchwald SL. Org. Lett. 2002, 4: 973 -
2d
Aranyos A.Old DW.Kiyomori A.Wolfe JP.Sadighi JP.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 4369 -
2e
Mann G.Hartwig JF. Tetrahedron Lett. 1997, 46: 8005 - 3
Lindley J. Tetrahedron 1984, 40: 1433 - 4
Fanta PE. Synthesis 1974, 9 - 5
Gujadhur R.Venkataraman D. Synth. Commun. 2001, 31: 2865 - 6
Hartwig JF. Pure. Appl. Chem. 1999, 71: 1417 - 7
Torraca KE.Huang X.Parrish CE.Buchwald SL. J. Am. Chem. Soc. 2001, 123: 10770 - 8
Kwong FY.Klapars A.Buchwald SL. Org. Lett. 2002, 4: 581 - 9
Marcoux JF.Doye S.Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539 - 10
Blass BE. Tetrahedron 2002, 58: 9301 -
11a
Yamawaki J.Ando T.Hanafusa T. Chem. Lett. 1981, 1143 -
11b
Yadav VK.Kapoor KK. Tetrahedron 1996, 52: 3659 -
11c
Alloum BA.Villemin D. Synth. Commun. 1989, 19: 2567 -
11d
Kabalka GW.Wang L.Namboodiri V.Pagni RM. Tetrahedron Lett. 2000, 41: 5151 -
11e
Kabalka GW.Pagni RM.Hair CM. Org. Lett. 1999, 1: 1423 - 12
Hosseinzadeh R.Tajbakhsh M.Mohadjerani M.Mehdinejad H. Synlett 2004, 517 - 13
Ando T.Brown SJ.Clark JH.Cork DG.Hanafusa T.Lchihara J.Miller JM.Robertson MS. J. Chem. Soc., Perkin Trans. 2 1986, 1133 - 14
Schmittling EA.Sawyer JS. Tetrahedron Lett. 1991, 32: 7207