Metal-catalyzed alkylation of 1,1-dihalovinyl moiety commonly suffers from both a
lack of stereoselectivity and the overreaction leading to the dialkylation product.
The methodology described herein features a new pathway to alkylate stereoselectively
β,β-dichlorostyryl substrates to provide the Z-trisubstituted olefin only with fair to good yields. This cross-coupling reaction
bears on the smooth and photoinduced formation of a C-centered radical that engages
in a nickel-catalyzed organometallic cycle to form the key Csp2–Csp3 bond.
Key words
cross-coupling - stereoselective alkylation - radical - dichlorostyrenes - bis(catecholato)silicates
- dual catalysis - counterion - nickel
