Stereoselective palladium-catalyzed cross-coupling of (2-amido-1-phenylpropyl)zinc compounds with aryl bromides

Abstract

A controllable diastereoselective C(sp ²)-C(sp ³) Negishi coupling reaction of secondary benzylic zinc reagents with aryl bromides to form medicinally important 2-arylphenylethylamines was demonstrated. In the presence of Pd(OAc)₂ and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl(S-phos), open-chain(2-amido-1-phenylethyl)zinc reagent bearing a β-NHAc or NHCHO group undergoes coupling reaction to give syn-1-arylphenylethylamine mainly, whereas the zinc reagent bearing a sterically hindered β-amido group, for example NHCOC(CH₃)₂OTBS undergoes the coupling reaction to yield anti-1-arylphenylethylamines with a configuration inversion. In addition, a working mechanism for the stereoselective Negishi cross-coupling was also proposed.

Keywords

Palladium / Stereoselective / Negishi coupling / Benzylic zinc / 2-Arylphenylethylamine

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