Organozinc-Mediated Direct C-C Bond Formation via C-N Bond Cleavage of Ammonium Salts.

We report a direct cross-coupling reaction between diarylzinc (Ar2 Zn) and aryltrimethylammonium salts (ArNMe3 + ⋅- OTf) in the presence of LiCl, via C-N bond cleavage. The reaction takes place smoothly upon heating in THF without any external catalyst, enabling an efficient and chemoselective formation of biaryl products. Mechanistic studies indicate that the reaction proceeds through a single electron transfer route.