Photo Click Reaction of Acylsilanes with Indoles

Light-mediated coupling of acylsilanes with indoles is reported. This photo click reaction occurs under mild conditions (415 nm) mostly in quantitative yield and provides stable silylated N,O-acetals via light mediated siloxycarbene generation subsequent indole-N-H insertion. We show that this very efficient fully atom economic process can be applied to conjugate complex systems, as documented by the clicking carbohydrates indole alkaloids. The method also applicable conjugation polymer chains. linking acetal moiety readily cleaved it shown wavelength-selective cleavage acyl silanes bearing a second photoactive possible. successful polymerization/depolymerization sequence folding/unfolding process.