Base-mediated C-B bond activation of benzylic boronate for the rapid construction of β-silyl/boryl functionalized 1,1-diarylalkanes from aromatic alkenes.
Liuzhou GaoXinyi LiangLinke HeGuoao LiShengda ChenJia CaoJing MaGuoqiang WangShuhua LiPublished in: Chemical science (2023)
The effect of t BuOK on the existing state of benzylic boronates in the solution phase has been investigated in detail by NMR analysis and DFT calculations. It was determined that simply using an excess of t BuOK (2.0 equivalents) can result in the full deborylation of benzylic boronates to afford free benzyl potassium species. These mechanistic insights were leveraged for the facile construction of β-silyl/boryl functionalized 1,1-diarylalkanes from aromatic alkenes via the combination of base-mediated silylboration or diborylation of aromatic alkenes and nucleophilic-type reactions with various electrophiles. Based on further machine-learning-assisted screening, the scope of electrophiles for this transformation can be generalized to the challenging aromatic heterocycles. Late-stage functionalization performed on several drug-relevant molecules generates the highly valuable 1,1-diaryl framework.
Keyphrases
- amino acid
- machine learning
- quantum dots
- density functional theory
- magnetic resonance
- high resolution
- molecular dynamics
- molecular dynamics simulations
- artificial intelligence
- molecularly imprinted
- big data
- highly efficient
- gold nanoparticles
- reduced graphene oxide
- mass spectrometry
- electronic health record
- simultaneous determination
- tandem mass spectrometry