Copper-Catalyzed Etherification of Aryl Iodides Using KF/Al2O3: An Improved Protocol

Rahman Hosseinzadeh; Mahmood Tajbakhsh; Maryam Mohadjerani; Mohammad Alikarami

doi:10.1055/s-2005-865198

LETTER

Copper-Catalyzed Etherification of Aryl Iodides Using KF/Al₂O₃: An Improved Protocol

Rahman Hosseinzadeh*, Mahmood Tajbakhsh*, Maryam Mohadjerani, Mohammad Alikarami
Faculty of Basic Science, Mazandaran University, Babolsar, Iran
Fax: +98(11252)42002; e-Mail: r.hosseinzadeh@umz.ac.ir;

Abstract

All articles of this category

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

Full Text

References

<A NAME="RD28904ST-1A">1a</A> Simon J. Salzbrunn S. Suryaprakash GK. Petasis NA. Olah GA. J. Org. Chem. 2001, 66: 633

<A NAME="RD28904ST-1B">1b</A> Mann G. Hartwig JF. Tetrahedron Lett. 1997, 38: 8005

<A NAME="RD28904ST-1C">1c</A> Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998, 39: 2937

<A NAME="RD28904ST-1D">1d</A> Pulley SHR. Ratasen S. Vorogushin A. Swanson E. Org. Lett. 1999, 1: 1721

<A NAME="RD28904ST-1E">1e</A> Nicolaou KC. Boddy CNC. Natarajan S. Yue TY. Li H. Brase S. Ramanjulu JM. J. Am. Chem. Soc. 1997, 119: 3421

<A NAME="RD28904ST-1F">1f</A> Palucki M. Wolfe JP. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 3395

<A NAME="RD28904ST-2A">2a</A> Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

<A NAME="RD28904ST-2B">2b</A> Ma D. Cai Q. Org. Lett. 2003, 5: 3799

<A NAME="RD28904ST-2C">2c</A> Wolter M. Nordmann G. Job GE. Buchwald SL. Org. Lett. 2002, 4: 973

<A NAME="RD28904ST-2D">2d</A> Aranyos A. Old DW. Kiyomori A. Wolfe JP. Sadighi JP. Buchwald SL. J. Am. Chem. Soc. 1999, 121: 4369

<A NAME="RD28904ST-2E">2e</A> Mann G. Hartwig JF. Tetrahedron Lett. 1997, 46: 8005

<A NAME="RD28904ST-3">3</A> Lindley J. Tetrahedron 1984, 40: 1433

<A NAME="RD28904ST-4">4</A> Fanta PE. Synthesis 1974, 9

<A NAME="RD28904ST-5">5</A> Gujadhur R. Venkataraman D. Synth. Commun. 2001, 31: 2865

<A NAME="RD28904ST-6">6</A> Hartwig JF. Pure. Appl. Chem. 1999, 71: 1417

<A NAME="RD28904ST-7">7</A> Torraca KE. Huang X. Parrish CE. Buchwald SL. J. Am. Chem. Soc. 2001, 123: 10770

<A NAME="RD28904ST-8">8</A> Kwong FY. Klapars A. Buchwald SL. Org. Lett. 2002, 4: 581

<A NAME="RD28904ST-9">9</A> Marcoux JF. Doye S. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539

<A NAME="RD28904ST-10">10</A> Blass BE. Tetrahedron 2002, 58: 9301

<A NAME="RD28904ST-11A">11a</A> Yamawaki J. Ando T. Hanafusa T. Chem. Lett. 1981, 1143

<A NAME="RD28904ST-11B">11b</A> Yadav VK. Kapoor KK. Tetrahedron 1996, 52: 3659

<A NAME="RD28904ST-11C">11c</A> Alloum BA. Villemin D. Synth. Commun. 1989, 19: 2567

<A NAME="RD28904ST-11D">11d</A> Kabalka GW. Wang L. Namboodiri V. Pagni RM. Tetrahedron Lett. 2000, 41: 5151

<A NAME="RD28904ST-11E">11e</A> Kabalka GW. Pagni RM. Hair CM. Org. Lett. 1999, 1: 1423

<A NAME="RD28904ST-12">12</A> Hosseinzadeh R. Tajbakhsh M. Mohadjerani M. Mehdinejad H. Synlett 2004, 517

<A NAME="RD28904ST-13">13</A> Ando T. Brown SJ. Clark JH. Cork DG. Hanafusa T. Lchihara J. Miller JM. Robertson MS. J. Chem. Soc., Perkin Trans. 2 1986, 1133

<A NAME="RD28904ST-14">14</A> Schmittling EA. Sawyer JS. Tetrahedron Lett. 1991, 32: 7207