Nickel-Catalyzed 1,2-Aminoarylation of Oxime Ester-Tethered Alkenes with Boronic Acids

A nickel-catalyzed 1,2-aminoarylation of oximeester-tethered alkenes with boronic acids was developed. A variety of pyrroline derivatives were synthesized in good yields via the successive formation of C(sp(3))-N and C(sp(3))-C(sp(2)) bonds. For cyclobutanone-derived oxime esters, the reaction provided aliphatic nitriles incorporating an aromatic group in the gamma-position. A mechanism involving iminyl radical and carbon-centered radical intermediates was proposed.