Journal of Organometallic Chemistry p. 413 - 420 (1991)
Update date:2022-08-04
Topics:
Munz, Christina
Stephan, Constantin
Dieck, Heindirk tom
With diazadiene (dad = RN=CR'-CR'=NR) as co-ligand the palladacyclopent-2-enes 3 formed by direct coupling of a 1-alkene and an acetylenedicarboxylic acid ester can be trapped.With activated 1-alkenes such as allylic alcohols the reaction becomes catalytic, yielding linear addition-products 4-11 from two molecules of the alkene and one molecule of the alkyne; no simple reductive elimination occurs, but instead elimination of one mole of water takes place.Allylic esters react analogously but a cyclic 1:2-addition-product 15 (also formed by loss of the leaving group) is the main product.The elimination of the leaving group is probably the driving force of the reaction, since only β-H-transfer that make elimination possible are observed.
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