Rh-Catalyzed Coupling of Arylzinc Halides with (Iodomethyl)trimethylsilane

Significance

This work has two interesting features. First, it is a still rare example of a Rh-catalyzed cross-coupling reaction, which takes place according to a somewhat different mechanism, compared to the conventional Pd- and Ni-catalyzed processes and therefore shows a different selectivity. Second, this is a practical synthetic route to functionalized benzylic trimethylsilanes, starting from available aryl iodides, with a good tolerance to functional groups. Beside silanes, benzyltributylstannanes can be prepared from aryl iodides in a similar way.