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Updated: Sep 3, 2025
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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1,2-Silylpyridylation Reaction of Aryl Alkenes with Silylboronate
Liuzhou Gao1, Xueting Liu1, Guoao Li1
1Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. China.
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.
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