The role of halide salt additives has been investigated in the Negishi Reaction involving aryl zinc reagents. Diarylzincs readily transmetallate to Pd in relatively non-polar media (e.g., THF) with zero salt added and coupling proceeds. Arylzinc halides (ArZnX) fail to couple inTHF without salt, but do couple with it. However, unlike alkylzincs that form higher order zincates in order to facilitate transmetallation, all that is required with arylzincs in an increase in solvent dielectric as even ZnX2 works as an additive, which completely terminates alkylzinc coupling. The details of both coupling partners will be discussed in detail.

Mechanistic details of the Negishi reaction with both alkyl- and arylzinc coupling partners

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.