Electrochemical Synthesis of Functional Aryl- and Heteroarylchlorosilanes. Application to the Preparation of Donor−Acceptor or Donor−Donor Organosilicon Molecules

A variety of functional aryl- and heteroarylchlorosilanes were prepared by electrochemical reduction of halothiophenes, halofurans, halopyridines, and substituted aryl halides in the presence of a large excess of commercial organodi- or trichlorosilanes using an undivided cell, a sacrificial Mg or Al anode, a constant current density, and tetrabutylammonium bromide as the supporting electrolyte. New structures are described, and some examples of the use of these more elaborate chlorosilanes are given, particularly as interesting precursors for the preparation of polarized D−A and D−D organosilicon models.