Reductive anti-Dizincation of Arylacetylenes.

Arylacetylenes undergo anti-1,2-dizincation to afford trans-1,2-dizincioalkenes. The process employs sodium dispersion as a reducing agent and zinc chloride TMEDA complex as a reduction-resistant zinc electrophile. This reductive anti-dizincation contrasts with the conventional additive syn-dimetalation like silylzincation. The resulting dizincated alkenes undergo the cross-coupling to yield multi-substituted alkenes stereoselectively.