P,N,N-Pincer nickel-catalyzed cross-coupling of aryl fluorides and chlorides

Abstract

P,N,N-Pincer nickel complexes [Ni(Cl){N(2-R₂PC₆H₄)(2′-Me₂NC₆H₄)}] (R = Ph, 3a; R = Prⁱ, 3b; R = Cy, 3c) were synthesized and their catalysis toward the Kumada or Negishi cross-coupling reaction of aryl fluorides and chlorides was evaluated. Complex 3a effectively catalyzes the cross-coupling of (hetero)aryl fluorides with aryl Grignard reagents at room temperature. Complex 3a also catalyzes the cross-coupling of (hetero)aryl chlorides and arylzinc reagents at 80 °C with low catalyst loadings and good functional group compatibility.