Arylsilane oxidation--new routes to hydroxylated aromatics.

@article{Bracegirdle2010ArylsilaneOR,
  title={Arylsilane oxidation--new routes to hydroxylated aromatics.},
  author={Sonia Bracegirdle and Edward A. Anderson},
  journal={Chemical communications},
  year={2010},
  volume={46 20},
  pages={
          3454-6
        }
}
An efficient route to hydroxylated aromatics has been developed, via the oxidation of aryl organosilanes under functional group-tolerant and relatively mild conditions, using sub-stoichiometric amounts of fluoride promoters. 

Figures and Tables from this paper

Microwave-assisted copper-catalyzed hydroxylation of aryl halides in water

A simple and efficient protocol for microwave-assisted copper-catalyzed hydroxylation of aryl halides is developed. A variety of phenols can be obtained in moderate to excellent yields of up to 95%.

Direct oxidation of the C(sp2)-C(sp3) bond from benzyltrimethylsilanes to phenols.

A novel pathway for direct conversion of benzylsilanes to phenols by oxidation with Na2S2O8 and oxygen is efficiently developed under mild and neutral conditions. The reaction shows good functional

Synthesis of phenols via fluoride-free oxidation of arylsilanes and arylmethoxysilanes.

TLDR
The effects of arene substituents and fluoride promoters on this process show that while electron-deficient arenes can undergo direct oxidation from the hydrosilane, electron-rich aromatics benefit from silane activation via oxidation to the methoxysilane using homogeneous or heterogeneous transition metal catalysis.

One-step preparation of functionalized (E)-vinylsilanes from aldehydes.

Functionalized (E)-vinylsilanes have been prepared in one step from a wide range of aldehydes, via a chromium(II)-mediated olefination with novel dihalomethylsilane reagents, in moderate to excellent

Radical–anion coupling through reagent design: hydroxylation of aryl halides

The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free

Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration.

Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity.

Facile Synthesis of Halogen Decorated para-/meta-Hydroxy­benzoates by Iridium-Catalyzed Borylation and Oxidation

TLDR
A facile preparation by iridium-catalyzed borylation of respective disubstituted benzoate esters followed by oxidation allows for the incorporation of halogens in the final hydroxybenzoates with substitution patterns not readily accessible by the traditional routes of aromatic functionalization.

Metal-catalyzed syntheses of abridged CDE rings of rubriflordilactones A and B.

The development of complementary palladium- and cobalt-catalyzed approaches to tricyclic arylsilanes suitable for elaboration into the CDE ring systems of rubriflordilactones A and B is reported.

Meta-Selective C-H Functionalization of Arylsilanes Using a Silicon Tethered Directing Group.

TLDR
Meta-selective C-H functionalization of arylsilanes using a Si-tethered directing group enables a selective alkenylation of arenes bearing a variety of functional groups and provides multisubstituted arenes efficiently.

Relay catalysis using a gold(I) complex/Brønsted acid binary system for the synthesis of bezoxasiloles

A strategy for the synthesis of synthetically useful benzoxasilole derivatives by combining a gold(I) complex/Bronsted acid binary system and a temporary silicon tether method has been developed that

References

SHOWING 1-10 OF 31 REFERENCES

Pd(II)-catalyzed hydroxylation of arenes with 1 atm of O(2) or air.

TLDR
Pd(II)-catalyzed ortho-hydroxylation of variously substituted benzoic acids under 1 atm of O(2) or air is achieved under nonacidic conditions to support a direct oxygenation of aryl C-H bonds with molecular oxygen.

C-H activation/borylation/oxidation: a one-pot unified route to meta-substituted phenols bearing ortho-/para-directing groups.

An efficient one-pot C-H activation/borylation/oxidation protocol for the preparation of phenols is described. This method is particularly attractive for the generation of meta-substituted phenols

Silafunctional compounds in organic synthesis. Part 20. Hydrogen peroxide oxidation of the silicon-carbon bond in organoalkoxysilanes

Scission oxydante de (diethoxy methyl octyl) silane par H 2 O 2 et conduisant a l'octanol-1

Directed hydroxylation of aromatics

Hydroxylation de diethylamides d'acides benzoique, acrisique, o-toluique, naphtoique-1 et trimethoxy benzoique

Oxidation of carbon-silicon bonds: the dramatic advantage of strained siletanes.

TLDR
This work reports on the use of siletanes as substrates for the oxidation of carbon-silicon bonds, which are easy to handle yet susceptible to rapid ring opening and oxidation upon exposure to aqueous fluoride and peroxide.

A palladium-mediated cascade cyclisation approach to the CDE cores of rubriflordilactone A and lancifodilactone G.

Palladium-mediated cascade cyclisation reactions have been applied to the synthesis of the CDE-ring cores of two anti-HIV natural products, rubriflordilactone A and lancifodilactone G.

TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines.

It is shown that the TBDPS protecting group can serve as an efficient phenyl group donor for o-bromophenols via Pd-catalyzed C-H arylation followed by a routine TBAF deprotection of the resulting

The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans.

TLDR
It is demonstrated that substituted benzofurans can be prepared efficiently via a Pd-catalyzed phenol formation/cyclization protocol starting from 2-chloroaryl alkynes.