The Synthetic Routes of (9,10-di(naphthalene-1-yl)anthracen-2-yl)boronic acid

(9,10-di(naphthalene-1-yl)anthracen-2-yl)boronic acid, also known as 9,10-bis(2,3-dihydroanthracen-9-yl)anthracene-2,9-boronic acid, is a synthetic compound that has garnered interest in the chemical industry due to its potential applications in various fields.
This article will discuss the synthetic routes of this compound, which can be broadly classified into three categories: directboration, displacement borane reduction, and Suzuki-Miyaura boronation.

Directboration

The directboration route involves the reaction of boric acid with an appropriate boronic acid derivative in the presence of a Lewis acid catalyst.
The reaction typically takes place in an inert solvent, such as ether or THF.
The reaction can be carried out at room temperature or at an elevated temperature, depending on the reactants and the catalyst used.

One of the most commonly used directboration protocols involves the reaction of boric acid with 2,3-dimethyl-9,10-di(2,3-dihydroanthracen-9-yl)anthracene-2,9-boronic acid, which is a commonly available boronic acid derivative.
The reaction typically proceeds via a free radical mechanism, with the Lewis acid catalyst facilitating the reaction by abstracting a hydrogen atom from the boronic acid derivative and forming a metal-boron bond.

Displacement Borane Reduction

The displacement borane reduction route involves the reduction of a borate ester or borate amide with a reducing agent, such as borane or diazabicyclo[2.
2.
2]octane (DABCO), in the presence of a catalyst, such as sodium hydride or cinchona aldehyde.
The reaction typically takes place in a polar solvent, such as THF or DMF, and can be carried out at room temperature or at an elevated temperature, depending on the reactants and the catalyst used.

One of the most commonly used displacement borane reduction protocols involves the reduction of 9,10-di(2,3-dihydroanthracen-9-yl)anthracene-2,9-boronic acid with borane in the presence of sodium hydride.
The reaction typically proceeds via a reduction of the borate ester to form a new boron-carbon bond, with the reducing agent facilitating the reaction by removing a hydrogen atom from the boron atom.

Suzuki-Miyaura Boronation

The Suzuki-Miyaura boronation route involves the reaction of a boronic acid derivative with a phenylborane species in the presence of a palladium catalyst, such as tetrakis(triphenylphosphine)palladium(0), and a base, such as sodium carbonate.
The reaction typically takes place in an inert solvent, such as toluene or xylene, and can be carried out at room temperature or at an elevated temperature, depending on the reactants and the catalyst used.

One of the most commonly used Suzuki-Miyaura protocols involves the reaction of 2-(dibutylamino)anthracene-9,10-di(2,3-dihydroanthracen-9-yl)boronic acid with phenylborane in the presence of tetrakis(triphenylphosphine)palladium(0) and sodium carbonate.
The reaction typically proceeds via a borylation of the boronic acid derivative, with the palladium catalyst facilitating the reaction by forming a metal-boron bond and the base facilitating the reaction by activating the hydrogen atom of the boronic acid derivative.

Applications

(9,10-di(naphthalene-1-yl