Cyclometalation of arylazo compounds. Part 2Regioselectivity of the Cyclopalladation of Some Substituted 1‐Arylazonaphthalenes. 2nd Communication on Compounds with a Metal‐Arene σ‐Bond

Abstract

Abstract A variety of cyclopalladated 1‐arylazonaphthalenes is described, where ortho ‐palladation occurs at C(2) in the naphthyl ring or at C(2′ or 6′) in the phenyl moiety. Two examples of Peri ‐cyclopalladation at C(8) in the naphthyl ring are presented. The electronic and steric‐influences of substituents at either arene moiety on the relative basicities of the azo‐N‐atoms and the relative nucleophilicities of the potential palladation sites C(2), C(2′ or 6′), and C(8) are discussed qualitatively in order to rationalize the observed regioselectivity.