1,2-Silylpyridylation Reaction of Aryl Alkenes with Silylboronate
Liuzhou Gao, Xueting Liu, Guoao Li, Shengda Chen, Jia Cao, Guoqiang Wang, Shuhua Li
Abstract
A metal-free silyl-pyridylation of alkenes using silyl boronates and B2pin2 through a pyridine-mediated B-interelement activation has been demonstrated, which provides a practical strategy for a variety of C4-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.
Topics & Concepts
ChemistryArylCombinatorial chemistryOrganic chemistryStereochemistryAlkylOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsChemical Synthesis and Analysis