1,2-Silylpyridylation Reaction of Aryl Alkenes with Silylboronate

A metal-free silyl-pyridylation of alkenes using silyl boronates and B(2)pin(2) through a pyridine-mediated B-interelement activation has been demonstrated, which provides a practical strategy for a variety of C-4-silylalkylated pyridines. DFT calculations and control experiments show that the reaction proceeds through a silyl radical addition/radical-radical coupling sequence. This protocol features a broad substrate scope and excellent functional group compatibility, and thus it showcases great potential in the late-stage modification of bioactive molecules.

Automated summary

A metal-free silyl-pyridylation method for the synthesis of C-4-silylalkylated pyridines has been demonstrated. This method proceeds through a silyl radical addition/radical-radical coupling sequence and exhibits a broad substrate scope and excellent functional group compatibility, making it suitable for late-stage modification of bioactive molecules.