A highly efficient and scalable method for synthesizing novel silylated heterocycles with potential applications in medicinal chemistry, fragrances, and materials is reported. The process involves NiBr2bipy-catalyzed electrochemical intramolecular hydrosilylation of alkenes, converting a variety of arylsilanes with high regioselectivity. The Si-H group exclusively adds to the carbon-carbon double bond via a 5-exo-trig cyclization. The reaction employs a sacrificial anode process, requiring only a "catalytic" amount of electricity and can therefore be readily scaled up for gram-scale synthesis. Mechanistic investigations, such as cyclic voltammetry, corroborate the proposed mechanism.
Reboli et al. (Mon,) studied this question.