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Synthesis 2004(9): 1307-1314
DOI: 10.1055/s-2004-822363
DOI: 10.1055/s-2004-822363
PAPER
© Georg Thieme Verlag Stuttgart · New York
GaCl3-Catalyzed α-Ethenylation Reaction of Ketone
Further Information
Received
20 January 2004
Publication Date:
12 May 2004 (online)
Publication History
Publication Date:
12 May 2004 (online)
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Abstract
In the presence of catalytic amounts of GaCl3 (10 mol%) and 2,6-di(t-butyl)-4-methylpyridine (10 mol%), five- or six-membered ring ketones possessing α,α′-disubstituents are ethenylated at the α-carbon with triethylsilylethyne at 180 °C. The roles of the base are to inhibit decomposition of the products and to promote protodegallation of the organogallium intermediates.
Keywords
catalytic reaction - α-ethenylation - GaCl3 - cyclic ketone - silylethyne
- 1
Millard AA.Rathke MW. J. Am. Chem. Soc. 1977, 99: 4833 - 2
Chieffi A.Kamikawa K.Åhman J.Fox JM.Buchwald SL. Org. Lett. 2001, 3: 1897 - 3
Seefelder M. Liebigs Ann. Chem. 1962, 652: 107 -
4a
Makosza M.Czyzewsky J.Jawdosiuk M. Org. Synth. 1976, 55: 99 -
4b
Makosza M. Tetrahedron Lett. 1966, 45: 5489 - 5
Tzalis D.Knochel P. Angew. Chem. Int. Ed. 1999, 38: 1463 - 6
Nakamura M.Endo K.Nakamura E. J. Am. Chem. Soc. 2003, 125: 13002 -
7a
Yamaguchi M.Tsukagoshi T.Arisawa M. J. Am. Chem. Soc. 1999, 121: 4074 -
7b
Arisawa M.Miyagawa C.Yamaguchi M. Synthesis 2002, 138 - 8
Arisawa M.Akamatsu K.Yamaguchi M. Org. Lett. 2001, 3: 789 - 9
Arisawa M.Miyagawa C.Yoshimura S.Kido Y.Yamaguchi M. Chem. Lett. 2001, 1080 - 10 We reported a catalytic ethenylation reaction of phenols using SnCl4:
Kobayashi K.Yamaguchi M. Org. Lett. 2001, 3: 241