Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Abstract

Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C–O bond cleavage was performed. Reaction of (<i>E</i>)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (<i>E</i>)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (<i>E</i>)-(prop-1-ene-1,3-diyl)­dibenzenes or 3-aryl/alkenyl-substituted (<i>E</i>)-(but-1-enyl)­benzene. Reaction of allyl alcohol with <i>p</i>-Me₂NC₆H₄ZnCl resulted in a mixture of normal coupling product 4-allyl-<i>N,N</i>-dimethylaniline and its isomerized product <i>N,N</i>-dimethyl-4-(prop-1-en-1-yl)­aniline