Contrary to the traditional implementation as a difluoromethyl group and recently disclosed role of C1 synthons in synthetic organic chemistry, difluorocarbene (:CF 2 ) is reported herein to proceed unprecedented atom recombination as both C1 synthon and F1 reagent simultaneously to render valuable 3-fluorinated oxindoles from 2aminoarylketones. The reaction does not require any catalyst and features a broad range of substrate scope with good functional group compatibility and ease of execution. This transformation could be employed to the quickconstructions of certain bioactive molecule derivatives. The mechanistic experiments and DFT calculations indicate that this atom recombination reaction of difluorocarbene for the synthesis of 3-fluorinated oxindoles may involve a rearrangement process of epoxide intermediates.
gem-Difluoroalkenyl boronates are attractive synthons
for constructing diverse gem-difluoroalkenes and
organoboron compounds. However, the strategies for the construction
of gem-difluorohomoallyl boronates has scarcely been
described. Herein, we develop an efficient protocol for the construction
of gem-difluorohomoallylic boronates through a Ni-catalyzed
radical-promoted defluoroalkylborylation of α-trifluoromethyl
alkenes with α-haloboronates under mild conditions. This reaction
features a broad substrate scope with good functional group tolerance
and diverse transformations.
An efficient nickel-catalyzed deoxygenative silylation reaction of aromatic amides with silylboranes in the presence of a Sm/SmI 2 system for the construction of α-aminosilanes is described. This strategy provides a direct method for synthesizing α-aminosilanes with high efficiency and good functional group compatibility and includes readily accessible starting materials and valuable products.
A radical-induced 1,2-α-boryl migration through radical polar crossover reactions has been described. In this work, in situ formed vinyldiboron "ate" complexes from alkenyl Grignard reagent and diborylalkanes react with commercial radical precursors under light initiation. This three-component process enables diborylation of alkene. This protocol features high atom economy, a broad substrate scope as well as good functional group toleration with mild conditions.
Herein we present a diastereoselective addition of arylboronic acids to α-keto N-tert-butanesulfinyl aldimines catalyzed by Rh(I) catalyst. This reaction provides a practical method to deliver valuable chiral α-amino ketones with...
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