Pd(II)-Catalyzed C-H Silylation of o-Alkynylanilines Initiated by an Aminopalladation To Access Disilylated 2-Phenyl-1H-indoles

Herein a Pd(II)-catalyzed C-H silylation of o-alkynylanilines with hexamethyldisilane for the synthesis of disilylated 2-phenyl-1H-indoles is reported. In this reaction, o-alkynylanilines undergo an aminopalladation, C-H activation, and dealkylation sequence to form five-membered C,C-palladacycles, which then couple with hexamethyldisilane to construct one C-N bond and two C-Si bonds. This method provides an alternative strategy for C-H silylation.

Automated summary

Here, a Pd(II)-catalyzed C-H silylation of o-alkynylanilines with hexamethyldisilane for the synthesis of disilylated 2-phenyl-1H-indoles is reported. This method involves a sequence of aminopalladation, C-H activation, and dealkylation to form five-membered C,C-palladacycles, which then react with hexamethyldisilane to construct one C-N bond and two C-Si bonds. It provides an alternative strategy for C-H silylation.