Copper-free synthesis of skipped diynes via cross-coupling reactions of alkynylalanes with propargylic electrophiles
Alkynylalanes provide a new, copper-free route to skipped diynes when combined with propargylic electrophiles bearing an aluminum-complexing leaving group. The reaction is mild, efficient, and, in contrast to copper-mediated methods, highly regioselective
Kessabi, Jilali,Beaudegnies, Renaud,Jung, Pierre M. J.,Martin, Benjamin,Montel, Florian,Wendeborn, Sebastian
The tungsten benzylidyne complex [PhC≡W{OSi(OtBu)3} 3] efficiently catalyzes the metathesis of conjugated diynes and ring-closing diyne metathesis (see scheme). Although this reaction implies C-C single-bond activation, 13C labeling studies reveal that it proceeds by classical alkylidyne group exchange and involves cleavage and formation of carbon-carbon triple bonds. Copyright
Lysenko, Sergej,Volbeda, Jeroen,Jones, Peter G.,Tamm, Matthias
supporting information; experimental part
p. 6757 - 6761
(2012/08/13)
A convenient, high-yielding copper-free synthesis of skipped 1,4-diynes
Alkynylalanes were found to react efficiently with propargylic electrophiles, such as propargyl mesylates and propargyl diethylphosphates. The reaction proceeds with high regioselectivity and does not require copper or any other transition metal. Georg Th
Kessabi, Jilali,Beaudegnies, Renaud,Jung, Pierre M. J.,Benjamin Martin, Florian Montel,Wendeborn, Sebastian
p. 655 - 659
(2008/12/21)
CROSS-COMBINATION OF MAGNESIUM DIACETYLENIDES WITH ORGANIC HALIDES CATALYZED BY TRANSITION METALS COMPLEXES
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Dzhemilev, U. M.,Saraev, R. A.,Vyrypaev, E. M.,Ibragimov, A. G.
p. 1888 - 1892
(2007/10/02)
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