Synthesis of a,a-diaryl nitriles by radical nucleophilic substitution

TOMAS C. TEMPESTI; ADRIANA B. PIERINI; MARIA T. BAUMGARTNER

ROYAL SOC CHEMISTRY

Lugar: London; Año: 2012 vol. 36 p. 597 - 597

he present study shows that the anion of 2-naphthylacetonitrile is substituted selectively at its Cα by aromatic halides, through a radical nucleophilic substitution mechanism, to give the corresponding α,α-diaryl nitriles in good yields. The regioselectivity of this ambident nucleophile changes with the steric hindrance at the radical centre from the aromatic substrate. The selectivity observed was investigated through a computational model of the key reaction step.