Direct Access to α-Aminosilanes Enabled by Visible-Light-Mediated Multicomponent Radical Cross-Coupling

alpha-Aminosilanes are an important class of organic compounds that show biological activity. In this communication, a new approach to alpha-aminosilanes that utilizes photoredox catalysis to enable three-component coupling of organo(tristrimethylsilyl)silanes with feedstock alkylamines and aldehydes is presented. A wide range of highly functionalized alpha-aminosilanes can be obtained in good yields under mild conditions. Both primary amines and secondary amines are compatible with this transformation. Moreover, optically pure alpha-aminosilanes are accessible by using chiral amines. Mechanistic studies indicate that reactions proceed through radical/radical cross-coupling of silyl radicals with alpha-amino alkyl radicals.

Automated summary

A new approach for the synthesis of alpha-aminosilanes using photoredox catalysis was presented, providing highly functionalized products in good yields under mild conditions. Both primary and secondary amines can be used for this transformation, and optically pure alpha-aminosilanes can be obtained by using chiral amines. Mechanistic studies indicate that the reactions proceed through radical/radical cross-coupling of silyl radicals with alpha-amino alkyl radicals.