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-00000083.xml
Synlett 2005(11): 1767-1770
DOI: 10.1055/s-2005-871543
DOI: 10.1055/s-2005-871543
CLUSTER
© Georg Thieme Verlag Stuttgart · New York
CuI/N,N-Dimethylglycine-Catalyzed Cross-Coupling Reaction of Vinyl Halides with Phenols and its Application to the Assembly of Substituted Benzofurans
Further Information
Received
28 March 2005
Publication Date:
14 June 2005 (online)
Publication History
Publication Date:
14 June 2005 (online)

Abstract
CuI-catalyzed coupling reaction of vinyl halides and phenols occurs at 60-90 °C with N,N-dimethylglycine hydrochloride as the additive, giving vinyl aryl ethers in good yields. The cross-coupling products formed from o-iodophenols and vinyl iodides are converted into substituted benzofurans via an intramolecular Heck reaction.
Key words
cross-coupling - vinyl aryl ethers - vinyl halides - benzofuran
- 1
Comprehensive Polymer Science
Vol. 3:
Allen G. Pergamon Press; New York: 1989. -
2a
Diaz-Requejo M.DiSalvo D.Brookhard M. J. Am. Chem. Soc. 2003, 125: 2038 -
2b
Boger DL.Corbett WL.Curren TT.Kasper AM. J. Am. Chem. Soc. 1991, 113: 1713 -
2c
Henke BR.Aquino CJ.Birkemo LS.Croom DK.Dougherty RW.Ervin GN.Grizzle MK.Hirst GC.James MK.Johnson MF.Queen KL.Sherrill RG.Sugg EE.Suh EM.Szewczyk JW.Unwalla RJ.Yingling J.Willson TM. J. Med. Chem. 1997, 40: 2706 ; and references cited therein -
3a
Christol H.Cristau H.-J.Soleiman M. Synthesis 1975, 736 -
3b
Reppe W. Ann. Chim. 1956, 601: 84 - 4
Okimoto Y.Sakaguchi S.Ishii Y. J. Am. Chem. Soc. 2002, 124: 1590 - 5
Crivello JV.Kong S. J. Org. Chem. 1998, 63: 6745 - For Pd-catalyzed methods see:
-
6a
Mann G.Hartwig JF. Tetrahedron Lett. 1997, 46: 8005 -
6b
Aranyos A.Old DW.Kiyomori A.Wolfe JP.Sadighi JP.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 4369 ; and references cited therein - For Cu-catalyzed methods see:
-
7a
Cristau H.-J.Cellier PP.Hamada S.Spindler J.-F.Taillefer M. Org. Lett. 2004, 6: 913 -
7b
Ma D.Cai Q. Org. Lett. 2003, 5: 3799 -
7c
Buck E.Song ZJ.Tschaen D.Dormer PG.Volante RP.Reider PJ. Org. Lett. 2002, 4: 1623 -
7d
Gujadhur RK.Bates CG.Venkataraman D. Org. Lett. 2001, 3: 4315 -
7e
Palomo C.Oiarbide M.Lopez R.Gomez-Bengoa E. Chem. Commun. 1998, 2091 -
7f
Marcoux J.-F.Doye S.Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539 - 8
Wan Z.Jones CD.Koenig TM.Pu YJ.Mitchell D. Tetrahedron Lett. 2003, 44: 8257 - 9
Willis MC.Taylor D.Gillmore AT. Chem. Commun. 2003, 2222 - 10
Nordmann G.Buchwald SL. J. Am. Chem. Soc. 2003, 125: 4978 -
11a
Ma D.Zhang Y.Yao J.Wu S.Tao F. J. Am. Chem. Soc. 1998, 120: 12459 -
11b
Ma D.Cai Q.Zhang H. Org. Lett. 2003, 5: 2453 -
11c
Ma D.Cai Q. Synlett 2004, 128 -
11d
Zhu W.Ma D. Chem. Commun. 2004, 888 -
11e
Cai Q.Zhu W.Zhang H.Zhang Y.Ma D. Synthesis 2005, 496 -
11f
Zhu W.Ma D. J. Org. Chem. 2005, 71: 2696 - 12
Pan X.Cai Q.Ma D. Org. Lett. 2004, 6: 1809 - For reviews see:
-
13a
Horton DA.Bourne GT.Smythe ML. Chem. Rev. 2003, 103: 893 -
13b
Hou X.-L.Yang Z.Wong HNC. Prog. Heterocycl. Chem. 2002, 14: 139 - For selected recent examples see:
-
13c
Willis MC.Taylor D.Gillmore AT. Org. Lett. 2004, 6: 4755 -
13d
Miyata O.Takeda N.Naito T. Org. Lett. 2004, 6: 1761 - 14 For a review see:
Beletskaya IP.Cheprakov AV. Chem. Rev. 2000, 100: 3009 - 15
Jeffery T. Tetrahedron 1996, 52: 10113