6315-97-5Relevant articles and documents
Nickel-catalyzed regio- and stereoselective reductive coupling of Oxa- and azabicyclic alkenes with enones and electron-rich alkynes
Mannathan, Subramaniyan,Cheng, Chien-Hong
, p. 2239 - 2246 (2014)
A nickel-catalyzed regio- and stereoselective reductive coupling of oxa- and azabicyclic alkenes with activated alkenes and electron-rich alkynes is described. Thus, 7-oxabenzonorbornadienes underwent reductive coupling with various vinyl ketones such as ethyl, methyl, propyl and α-methyl- substituted vinyl ketones, in the presence of a nickel(II) iodide (NiI 2), zinc (Zn), and water catalyst system in acetonitrile at 50 °C for 14 h to afford 2-alkylnaphthalenes in good to excellent yields. Under similar reaction conditions, 7-azabenzonorbornadiene derivatives provided cis-2-alkyl-1,2-dihydronaphthalene derivatives in high yields. On the other hand, the nickel(II) iodide, tris(4-fluorophenyl)phoshine [P(4-FC 6H4)3] and zinc catalyst system successfully catalyzed the reductive coupling reaction of electron-rich alkynes, with 7-aza- and 7-oxabenzonorbornadienes to give cis-2-alkenyl-1,2-dihydronaphthalene derivatives in good to excellent yields. In the reaction, a mild reducing agent (zinc) and simple hydrogen source (water) were used.
