Catalyst-free carbosilylation of alkenes using silyl boronates and organic fluorides via selective C-F bond activation

Jun Zhou, Bingyao Jiang, Yamato Fujihira, Zhengyu Zhao, Takanori Imai and Norio Shibata ()
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Jun Zhou: Nagoya Institute of Technology, Gokiso
Bingyao Jiang: Nagoya Institute of Technology, Gokiso
Yamato Fujihira: Nagoya Institute of Technology, Gokiso
Zhengyu Zhao: Nagoya Institute of Technology, Gokiso
Takanori Imai: Nagoya Institute of Technology, Gokiso
Norio Shibata: Nagoya Institute of Technology, Gokiso

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract A regioselective carbosilylation of alkenes has emerged as a powerful strategy to access molecules with functionalized silylated alkanes, by incorporating silyl and carbon groups across an alkene double bond. However, to the best of our knowledge, organic fluorides have never been used in this protocol. Here we disclose the catalyst-free carbosilylation of alkenes using silyl boronates and organic fluorides mediated by tBuOK. The main feature of this transformation is the selective activation of the C-F bond of an organic fluoride by the silyl boronate without undergoing potential side-reactions involving C-O, C-Cl, heteroaryl-CH, and even CF3 groups. Various silylated alkanes with tertiary or quaternary carbon centers that have aromatic, hetero-aromatic, and/or aliphatic groups at the β-position are synthesized in a single step from substituted or non-substituted aryl alkenes. An intramolecular variant of this carbosilylation is also achieved via the reaction of a fluoroarene with a ω-alkenyl side chain and a silyl boronate.

Date: 2021
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DOI: 10.1038/s41467-021-24031-w

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