Photocatalytic Synthesis of Diarylmethyl Silanes via 1,6-Conjugate Addition of Silyl Radicals to p‑Quinone Methides

A novel photocatalytic method for the preparation of diarylmethyl silanes was reported through silyl radicals addition strategy to p-QMs (p-quinone methides). This protocol could tolerate a variety of functional groups affording the corresponding silylation products with moderate to excellent yields...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 5; pp. 3567 - 3576
Main Authors Luo, Cong, Lu, Wen-hua, Wang, Guo-qin, Zhang, Zheng-bing, Li, Hai-qiong, Han, Pan, Yang, Dan, Jing, Lin-hai, Wang, Chen
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.03.2022
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Summary:A novel photocatalytic method for the preparation of diarylmethyl silanes was reported through silyl radicals addition strategy to p-QMs (p-quinone methides). This protocol could tolerate a variety of functional groups affording the corresponding silylation products with moderate to excellent yields. The resulting silylation products could be easily converted into a series of bioactive GPR40 agonists and useful p-QMs precursors for the synthesis of compounds possessing both quaternary carbon centers and silicon substituents through simple operation. A plausible mechanism of silyl radicals to p-QMs was proposed on the basis of experimental results and previous literature.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c03125