Low pressure vinylation of aryl and vinyl halides via Heck-Mizoroki reactions using ethylene

Aryl bromides and iodides in the presence of catalytic amounts of a palladacycle derived from acetophenone oxime and 2 equiv of potassium acetate react with ethylene under ambient pressure (15-30 psi) to give the corresponding vinylarenes. The reactions work with both electron-deficient and electron-rich aryl compounds and tolerate wide variety of common functional groups. Vinyl bromides lead to 1,3-dienes in moderate yields.

Graphical abstractDownload full-size image