Abstract
A controllable diastereoselective C(sp2)-C(sp3) Negishi coupling reaction of secondary benzylic zinc reagents with aryl bromides has been demonstrated for the first time, forming medicinally important 1-arylphenylethylamines. In the presence of Pd(OAc)2 and S-phos, open-chain (2–amido-1-phenylethyl)zinc reagents bearing a β-NHAc or NHCHO group underwent cross-coupling reaction to give syn 1-arylphenylethylamine as the major products, whereas the zinc reagents bearing a sterically hindered β-NHCOC(CH3)2OTBS group specifically yielded anti 1-arylphenylethylamines.
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