Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 2
538
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Copper-Catalyzed Coupling of Aryl Halides with Terminal Alkynes in the Presence of KF/Al2O3

, , &
Pages 282-288 | Received 16 Mar 2009, Published online: 29 Dec 2009

REFERENCES

  • Sonogashira , K. ; Tohda , Y. ; Hagihara , N. A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines . Tetrahedron Lett. 1975 , 16 ( 50 ), 4467 – 4470 .
  • Sonogashira , K. In Comprehensive Organic Synthesis ; B. M. Trost (Ed.) ; Pergamon Press : Oxford , 1999 ; vol. 3 , p. 521 .
  • (a) Diederich , F. ; Stang , P. J. Metal-Catalyzed Cross-Coupling Reactions ; Wiley-VCH : Weinheim , 1998 ; (b) Miyaura , N. Cross-Coupling Reaction ; Springer : Berlin , 2002 .
  • (a) Beauperin , M. ; Fayad , E. ; Amardeil , R. ; Cattey , H. ; Richard , P. ; Brandes , S. ; Meunier , P. ; Hierso , J. C. First copper(I) ferrocenyltetraphosphine complexes: Possible involvement in Sonogashira cross-coupling reaction? Organometallics 2008 , 27 , 1506 – 1513 ; (b) Chinchilla , R. ; Najera , C. The Sonogashira reaction: A booming methodology in synthetic organic chemistry . Chem. Rev. 2007 , 107 , 874 – 922 .
  • (a) Eckhardt , M. ; Fu , G. C. J. The first applications of carbene ligands in cross-couplings of alkyl electrophiles: Sonogashira reactions of unactivated alkyl bromides and iodides . J. Am. Chem. Soc. 2003 , 125 , 13642 – 13643 ; (b) Hill , L. L. ; Smith , J. M. ; Brown , W. S. ; Moore , L. R. ; Guevera , P. ; Pair , E. S. ; Porter , J. ; Chou , J. ; Wolterman , C. J. ; Craciun , R. ; Dixon , D. A. ; Shaughnessy , K. H. Neopentylphosphines as effective ligands in palladium-catalyzed cross-couplings of aryl bromides and chlorides . Tetrahedron 2008 , 64 , 6920 – 6934 .
  • (a) Lee , D. H. ; Qiu , H. ; Chao , M. H. ; Lee , M. I. ; Jin , M. J. Efficient Sonogashira coupling reaction catalyzed by palladium(II) β-oxoiminatophosphane complexes under mildconditions . Synlett 2008 , 1657 – 1660 ; (b) Cai , M. ; Sha , J. ; Xu , Q. MCM-41-supported bidentate phosphine palladium(0) complex: A highly active and recyclable catalyst for the Sonogashira reaction of aryl iodides . Tetrahedron 2007 , 63 , 4642 – 4647 .
  • (a) Okuro , K. ; Furuune , M. ; Enna , M. ; Miura , M. ; Nomura , M. Synthesis of aryl- and vinylacetylene derivatives by copper-catalyzed reaction of aryl and vinyl iodides with terminal alkynes . J. Org. Chem. 1993 , 58 , 4716 – 4721 ; (b) Ma , D. ; Liu , F. CuI-catalyzed coupling reaction of aryl halides with terminal alkynes in the absence of palladium and phosphine . Chem. Commun. 2004 , 1934 – 1935 ; (c) Guan , J. T. ; Yu , J. A. ; Chen , L. ; Weng , T. Q. ; Yuan , J. J. ; Liu , S. H. CuI/PPh3-catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes in water in the absence of palladium . Appl. Organometal. Chem. 2009 , 23 , 75 – 77 .
  • (a) Mao , J. ; Guo , J. ; Ji , S. J. CuBr/rac-BINOL-catalyzed Sonogashira reaction of terminal alkynes with aryl halides or arylboronic acids . J. Mol. Catal. A: Chem. 2008 , 284 , 85 – 88 ; (b) Tang , B. X. ; Wang , F. ; Li , J. H. ; Xie , Y. X. ; Zhang , M. B. Reusable Cu2O/PPh3/TBAB system for the cross-couplings of aryl halides and heteroaryl halides with terminal alkynes . J. Org. Chem. 2007 , 72 , 6294 – 6297 ; (c) Shao , L. X. ; Shi , M. Copper-catalyzed coupling reactions of alkenyl halides with alkynes in the absence of palladium and ligand . Tetrahedron 2007 , 63 , 11938 – 11942 .
  • Blass , B. E. KF/Al2O3-mediated organic synthesis . Tetrahedron 2002 , 58 , 9301 – 9320 .
  • (a) Alloum , A. B. ; Villemin , D. Potassium fluoride on alumina: An easy preparation of diazocarbonyl compounds . Synth. Commun. 1989 , 19 , 2567 – 2571 ; (b) Kabalka , G. W. ; Pagni , R. M. ; Hair , C. M. Solventless Suzuki coupling reactions on palladium-doped KF/Al2O3 . Org. Lett. 1999 , 1 , 1423 – 1425 ; (c) Wang , M. ; Li , P. ; Wang , L. Microwave irradiated solventless Sonogashira reaction on nickel(0) powder–doped KF/Al2O3 . Synth. Commun. 2004 , 34 , 2803 – 2812 .
  • (a) Hosseinzadeh , R. ; Tajbakhsh , M. ; Mohadjerani , M. ; Mehdinejad , H. Copper-catalyzed amidation of aryl iodides using KF/Al2O3: An improved protocol . Synlett 2004 , 1517 – 1520 ; (b) Hosseinzadeh , R. ; Tajbakhsh , M. ; Alikarami , M. Copper-catalyzed N-arylation of diazoles with aryl bromides using KF/Al2O3: An improved protocol . Tetrahdron Lett. 2006 , 47 , 5203 – 5205 ; (c) Hosseinzadeh , R. ; Tajbakhsh , M. ; Alikarami , M. Highly efficient copper-catalyzed formation of N-aryl diazoles using KF/Al2O3 . Synlett 2006 , 2124 – 2126 ; (d) Hosseinzadeh , R. ; Tajbakhsh , M. ; Alikarami , M. ; Mohadjerani , M. N-Arylation of N-H heterocycles with aryl bromides and aryl iodides using CuI and KF/Al2O3 . J. Heterocycl. Chem. 2008 , 45 , 1815 – 1818 ; (e) Hosseinzadeh , R. ; Tajbakhsh , M. ; Mohadjerani , M. ; Ghorbani , E. CuI-catalyzed coupling reactions of aryl iodides with amides using L-proline and KF/Al2O3 . Chin. J. Chem. 2008 , 26 , 2120 – 2124 ; (f) Hosseinzadeh , R. ; Golchoubian , H. ; Masoudi , M. Copper-catalyzed amidation of aryl iodides in the presence of various chelating ligands . J. Chin. Chem. Soc. 2008 , 55 , 649 – 653 ; (g) Hosseinzadeh , R. ; Sarrafi , Y. ; Mohadjerani , M. ; Mohammadpourmir , F. Copper-catalyzed arylation of phenylurea using KF/Al2O3 . Tetrahedron Lett. 2008 , 49 , 840 – 843 .
  • (a) Hosseinzadeh , R. ; Tajbakhsh , M. ; Mohadjerani , M. ; Alikarami , M. Copper-catalyzed etherification of aryl iodides using KF/Al2O3: An improved protocol. Synlett 2005, 1101–1104; (b) Hosseinzadeh , R. ; Tajbakhsh , M. ; Mohadjerani , M. ; Rezaei , P. ; Alikarami , M. Synthesis of diaryl ethers through the copper-catalyzed arylation of phenols with aryl iodides using KF/Al2O3 . Synth. Commun. 2008, 38, 3023–3031.
  • (a) Deng , W. ; Zou , Y. ; Wang , Y. F. ; Liu , L. ; Guo , Q. X. CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands . Synlett 2004 , 1254 – 1258 ; (b) Xie , X. ; Cai , G. ; Ma , D. CuI/L-proline-catalyzed coupling reactions of aryl halides with activated methylene compounds . Org. Lett. 2005 , 7 , 4693 – 4695 ; (c) Liu , F. ; Ma , D. Assembly of conjugated enynes and substituted indoles via CuI/amino acid–catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides . J. Org. Chem. 2007 , 72 , 4844 – 4850 .
  • Kabalka , G. W. ; Wang , L. ; Namboodiri , V. ; Pagni , R. M. Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted-benzo[b]furans, and 2-substituted-indoles . Tetrahedron 2001 , 57 , 8017 – 8028 .
  • Cheng , J. ; Sun , Y. ; Wang , F. ; Guo , M. ; Xu , J. H. ; Pan , Y. ; Zhang , Z. A copper- and amine-free Sonogashira reaction employing aminophosphines as ligands . J. Org. Chem. 2004 , 69 , 5428 – 5432 .
  • Furstner , A. ; Mathes , C. Alkyne cross metathesis reactions of extended scope . Org. Lett. 2001 , 3 , 221 – 223 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.