Aminomethylation of Oxabenzonorbornadienes via the Merger of Photoredox and Nickel Catalysis.
Abdoul G DialloDavid RoySylvain GaillardMark LautensJean-Luc RenaudPublished in: Organic letters (2020)
The first aminomethylation of oxabenzonorbornadienes using dual photoredox/nickel catalysis has been disclosed. This cascade reaction allowed the preparation of the cis-aminomethyl dihydronaphthalenols without any prefunctionalization or any use of nucleophilic organometallic species. The control of the regio- and stereoselectivity might be explained by a sequence involving insertion of nickel(0) into the C-O bond followed by the formation of a π-allyl intermediate.