108839-92-5Relevant articles and documents
Ni0-induzierte CC-Verknuepfungen von Phenylisocyanat mit cyclischen, fuenfgliedrigen Alkenen, katalytische Herstellung von β,γ-ungesaettigten Carbonsaeureaniliden
Hoberg, Heinz,Nohlen, Matthias
, p. 225 - 236 (2007/10/02)
Cycloalkenes with a five-membered cyclic system like bicyclooctene-2 (1a), 2,3-dihydrofuran (1b) and 2,5-dihydrofuran (1c) react with phenylisocyanate on a (Lig)Ni0-system (Lig = tricyclohexylphosphane) to form tricyclohexylphosphane-5-azanickelacyclopentan-4-one derivatives by oxidative 1 : 1 CC-coupling.It has been shown, that these complexes are intermediates of catalytic reactions in which only H-abstraction in β'-position outside the nickelaheterocyclic system takes place because of cis-configuration of this bi- or tricyclic metalla complexes.In this way β,γ-unsaturated carboxylic acid-anilides are obtained with high selectivity.Catalytic CC-coupling does not occur if the β'-position is occupied by an oxygen atom as shown in the metallacycle formed from 2,3-dihydrofuran, phenylisocyanate and (Lig)Ni0.