C-H Silylation of 2-Arylpyridine Derivatives by Using Iridium Catalyst and Phosphine-Borane Ligand

Iridium-catalyzed ortho-C-H silylation of 2-arylpyridine derivative with hydrosilane by using phosphine-borane ligand has been developed. A variety of 2-arylpyridines could be used for this reaction to give mono- and disilylated products in 81-99% yields. In this reaction, the length of linkage between phosphorus and boron plays an important role for the reaction to proceed. We consider that the nitrogen in 2-arylpyridine coordinates to Lewis acidic boron in the ligand and thus the iridium is led to an ortho-C-H bond to cleave it.

Automated summary

An iridium-catalyzed ortho-C-H silylation of 2-arylpyridine derivative with hydrosilane by using phosphine-borane ligand has been developed. This reaction yields mono- and disilylated products in 81-99% yields, using various 2-arylpyridines. The length of the linkage between phosphorus and boron is crucial for the reaction to proceed.