|Title||Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes|
|Publication Type||Journal Article|
|Year of Publication||2017|
|Authors||Desnoyer, AN, Geng, J, Drover, MW, Patrick, BO, Love, JA|
|Journal||CHEMISTRY-A EUROPEAN JOURNAL|
|Date Published||AUG 25|
Low-valent nickel is shown to preferentially isomerize mono-or disubstituted epoxides into their corresponding aldehydes. Experiments with tetrasubstituted epoxides demonstrate that these reactions proceed via reactive 2-nickelaoxetane intermediates, and that the oxidative addition step likely occurs with retention of configuration. The monosubstituted aldehyde isomerization products were found to rapidly react with HBpin to form boronate esters. These hydroboration reactions could be performed catalytically.