204444-15-5

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 

Downstream Products

• 91960-97-3 1,2-bis(3-bromophenyl)ethane-1,2-dione 
• 585-76-2 m-bromobenzoic acid 

Relevant academic research and scientific papers

CeCl3/Sm promoted pinacolic coupling of aromatic aldehydes and ketones

The pinacolic coupling of aromatic aldehydes and ketone was performed with cerium trichloride and samarium in THF at room temperature to afford the corresponding 1,2-diols in good yields.

Metal-free thermal organocatalytic pinacol coupling of arylaldehydes using an isonicotinate catalyst with bis(pinacolato)diboron

The metal-free thermal organocatalytic pinacol coupling of arylaldehydes has been developed. The intermolecular coupling of arylaldehydes catalyzed byt-butyl isonicotinate with bis(pinacolato)diboron as the co-reducing agent afforded 1,2-diphenylethane-1,2-diols. This reaction was also applicable to the intramolecular coupling of 1,1′-biphenyl-2,2′-dicarbaldehydes to afford 9,10-dihydrophenanthrene-9,10-diols. Various functional groups were tolerated under this coupling condition.

Bifunctional copper-based photocatalyst for reductive pinacol-type couplings

A bifunctional copper-based photocatalyst has been prepared that employs a pyrazole-pyridine ligand incorporating a sulfonamide moiety that functions as an intramolecular hydrogen-bond donor for a photochemical PCET process. In typical reductive PCET processes, the photocatalyst and H-bond donor must have an appropriate redox potential and pKa, respectively, to promote the PCET. When working in concert in a bifunctional catalyst such as Cu(pypzs)(BINAP)BF4, the pKa of the H-bond donor can have an acidity that is orders of magnitude less and still efficiently promote the PCET process. A reductive pinacol-type coupling can be performed using a base-metal derived photocatalyst to afford valuable diols (24 examples, 46-99% yield), from readily available aldehydes and ketones.

Mg/Triethylammonium formate: A useful system for reductive dimerization of araldehydes into pinacols; Nitroarenes into azoarenes and azoarenes into hydrazoarenes

Studies are reported which describes the effectiveness of triethylammonium formate in the presence of magnesium for the efficient intermolecular pinacol coupling using MeOH as solvent, Various aromatic carbonyls underwent smooth reductive coupling to give the corresponding I ,2-diols. A series of azo compounds were obtained by the reductive coupling of nitroaromatics while azo compounds were reduced to the corresponding hydrazoarenes by this system. There was no adverse effect on the other reducible and hydrogenolysable groups such as ether linkage, hydroxy and halogens. The reactions are clean, high yielding and inexpensive. All the reactions proceeded smoothly at ambient temperature.

Magnesium-induced pinacol coupling of aromatic aldehydes and ketones under ultrasound irradiation

The system of magnesium and magnesium iodide can reduce some aromatic aldehydes and ketones to the corresponding pinacols in good yields within 10-60 min at room temperature under ultrasound irradiation. Copyright Taylor & Francis, Inc.

Pinacol coupling reaction of aromatic aldehydes mediated by aqueous vanadium(II) solution under ultrasound irradiation

Pinacol coupling of aromatic aldehydes by aqueous vanadium(II) solution under ultrasound irradiation at room temperature can lead to the corresponding pinacols in 54-93% yields within 15-30 min. Copyright Taylor & Francis, Inc.

Carbon-carbon bond formation reaction promoted by cadmium in aqueous media

Promoted by metallic cadmium allylilic and propargyl bromides react smoothly with aldehydes in aqueous DMF to give homoallylic and homopropargyl alcohols in moderate to good yields. It can also promote pinacol coupling of aromatic aldehydes. The metallic cadmium is produced in situ by the reduction of CdCl2 · H2O with samarium metal.

Water accelerated Sm/TMSCl reduction system: Pinacolic coupling of aromatic carbonyl compounds and reductive dimerization cyclization of 1,1- dicyanoalkenes

By action of Sm/TMSCl in THF at room temperature, aromatic carbonyl compounds produce the corresponding 1,2-diols via reductive coupling reaction and 1,1-dicyanoalkenes produce the functionalized cyclopentenes through reductive dimerization followed by intramolecular cyclization in one-pot. The former gives approximately equal amounts of (dl)- and (meso)-1,2-diols and the later gives the major trans-form products. Added micro amounts of water to the system not only can accelerate the reaction, but also increase the yields of products. Moreover, only substoichiometric quantities of metallic samarium are employed.