Stereospecific Suzuki-Miyaura Coupling of Chiral α-(Acylamino)benzylboronic Esters with Inversion of Configuration

The first invertive B-alkyl Suzuki-Miyaura coupling has been achieved. The coupling of enantioenriched alpha-(acylamino)benzylboronic esters with aryl bromides and chlorides took place efficiently in toluene at 80 degrees C in the presence of Pd(dba)(2) (5 mol %), XPhos (10 mol %), K(2)CO(3) (3 equiv), and H(2)O (2 equiv). The reaction proceeded with inversion of configuration to give diarylmethanamine derivatives in high yields with high conservation of enantiomeric excesses.