title: Intramolecular carbonickelation of alkenes.
abstract: The efficiency of the intramolecular carbonickelation of substituted allylic ethers and amines has been studied to evaluate the influence of the groups borne by the double bond on this cyclization. The results show that when this reaction takes place, it affords only the 5-exo-trig cyclization products, viz. dihydrobenzofurans or indoles. Depending on the tethered heteroatom (O or N), the outcome of the cyclization differs. While allylic ethers are relatively poor substrates that undergo a side elimination and need an intracyclic double bond to proceed, allylic amines react well and afford indoline and indole derivatives. Finally, the synthesis of the trinuclear ACE core of a morphine-like skeleton was achieved by using NiBr2bipy catalysis.
authors.affiliation: Laboratoire COBRA, CNRS UMR 6014 & FR 3038, Université de Rouen, INSA de Rouen, 1 rue Tesnières, 76821 Mont St Aignan Cedex, France.
authors.forename: Rudy
authors.initials: R
authors.lastname: Lhermet
authors.forename: Muriel
authors.initials: M
authors.lastname: Durandetti
authors.forename: Jacques
authors.initials: J
authors.lastname: Maddaluno
keywords: Heck-type reaction; alkenes; carbometallation; carbonickelation; cyclization; nickel catalysis