Uncatalysed coupling of an activated aryl chloride with aryllithium and aryl Grignard reagents

Convenient Synthesis of Pharmacologically Active Ortho-Substituted Biaryl Oxazolines via the Suzuki Reaction

“…Adapting published methods based on oxazoline chemistry [5][6][7][8][9][10][11] and preparation of these biaryl oxazolines [12] resulted in multistep sequences, which often involved chromatographic separations and gave poor overall yields. Until now, these biaryl oxazolines have been synthesized by nucleophilic aromatic substitution on aryloxazolines, but we thought that these could also be prepared by the Suzuki coupling reaction.…”

The Meyers Reaction (1994-2010)

“…These efforts have focussed, in particular, on palladium-catalyzed cross-coupling processes such as the Suzuki [12] and Kumada [13] reactions for the preparation of biaryls, and re- lated processes such as the Heck or Negishi [14] reactions for the preparation of substituted arenes [15]. 2-Chlorophenyl oxazolines 20 undergo direct substitution reactions with both aryllithium reagents and aryl Grignard reagents in excess (4-8 equiv) without the need of a catalyst (Scheme 5) [16]. The coupling products 21 were obtained in fair to reasonable yields (40-78%), although the reactions with Grignard reagents required a larger amount of reagent and/or longer reaction times.…”