Group IB Organometallic Chemistry. XV. Arylcopper compounds ArnCun as intermediates in organometallic synthesis. One-step synthesis of triorganotin halides of the type Ar3SnX and Ar3-nRnSnX

Abstract

A new method for the one-step preparation of triorganotin halides is described. Triphenyltin halides are synthesized via the reaction of pure phenylcopper with SnX{4} or with Ph{2}SnX{2}. Me{2}NCH{2}, Me{2}N and OMe-substituted phenylcopper react with Me{2}(or Ph{2})SnBr{2} to give novel (substituted-phenyl)-diorganotin bromides in high yields. The selective arylation of tin halides by organocopper compounds is based upon the low reactivity of RCu towards the Sn@?X bond in triorganotin halides. The selectivity of the arylation by the corresponding phenyllithium derivatives is connected with intra- or inter-molecular Sn@?N (or O) coordination and/or of steric factors exerted by substituents ortho to the Sn@?C(phenyl) bond.