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Synfacts 2007(2): 0191-0191
DOI: 10.1055/s-2006-955804
DOI: 10.1055/s-2006-955804
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Copper-Free Synthesis of 1,4-Diynes
J. Kessabi, R. Beaudegnies, P. M. J. Jung, B. Martin, F. Montel, S. Wendeborn*
Syngenta Crop Protection, Basel, Switzerland
Further Information
Publication History
Publication Date:
23 January 2007 (online)
Significance
Methylene-bridged 1,4-diynes (‘skipped diynes’) are useful intermediates in the synthesis of complex organic molecules and natural products. The usual approach to these compounds involves the reaction between copper acetylides and propargylic electrophiles. This process is not completely regioselective and also not convenient for the industrial applications. The present reaction between alkynylalanes and propargylic mesylates does not require any transition-metal catalyst. The procedure is convenient and simple to perform.