1122065-36-4

Upstream product

• 3282-30-2 pivaloyl chloride 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 1533458-03-5 6-bromonaphthalen-2-yl pivalate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 183200-85-3 6-(4-methoxyphenyl)naphthalen-2-ol 

Downstream Products

• 1122065-50-2 2-(4-methoxyphenyl)-6-(2,4,5-trimethylphenyl)naphthalene 

Relevant academic research and scientific papers

Chemoselective Cross-Coupling between Two Different and Unactivated C(aryl)-O Bonds Enabled by Chromium Catalysis

We report here the first example of cross-coupling between two different and unactivated C(aryl)-O bonds with chromium catalysis. The combination of a low-cost Cr(II) salt, 4,4′-di-tert-butyl-2,2′-dipyridyl (dtbpy) as the ligand, and magnesium as the reductant shows high reactivity in promoting the reductive cross-coupling of aryl methyl ether derivatives with aryl esters by cleavage and coupling of two different C(aryl)-O bonds under mild conditions. The formation of active low-valent Cr species by reduction of CrCl2 with Mg can be considered, which prefers to initially activate the C(aryl)-O bond of phenyl methyl ether with the chelation help of dtbpy and an o-imine auxiliary. The subsequent consecutive reduction, second C(aryl)-O activation, and reductive elimination allow for the achievement of selective cross-coupling of C(aryl)-O/C(aryl)-O bonds.

Reductive Cross-Coupling between Unactivated C(aryl)-N and C(aryl)-O Bonds by Chromium Catalysis Using a Bipyridyl Ligand

Reductive cross-coupling between two chemically inert bonds remains a great challenge in synthetic chemistry. We report here the reductive cross-coupling between unactivated C(aryl)-N and C(aryl)-O bonds that was achieved by chromium catalysis. The simple and inexpensive CrCl2 salt, combined with important bipyridyl ligand and magnesium reductant, shows high reactivity in the successive cleavage of C(aryl)-N bonds of aniline derivatives and C(aryl)-O bonds of aryl esters, allowing the cross-coupling of these two unactivated and different bonds to occur in a reductive fashion to form a C(aryl)-C(aryl) bond. Mechanistic studies by deuterium-labeling experiments indicate that the C(aryl)-N bonds in anilines are preferentially cleaved by reactive Cr species, in which the ligation of bipyridyl with Cr by adopting a coordination model in 1:1 ratio can be considered.

Ni-Catalyzed Decarboxylative Cross-Coupling of Potassium Polyfluorobenzoates with Unactivated Phenol and Phenylmethanol Derivatives

A Ni-catalyzed decarboxylative cross-coupling of potassium polyfluorobenzoates with unactivated phenol and phenylmethanol derivatives is described. This novel transformation provides a practical and efficient protocol towards the synthesis of important polyfluorobiaryls and polyfluorinated diarylmethanes, and greatly enlarges the range of electrophiles utilized in decarboxylative coupling. Remarkably, preliminary mechanistic studies indicated the essential role of Zn(OAc)2 might lie in the enhancement of decarboxylation step. (Figure presented.).

Nickel-Catalyzed Synthesis of Primary Aryl and Heteroaryl Amines via C-O Bond Cleavage

A nickel-catalyzed protocol for the conversion of aryl and heteroaryl alcohol derivatives to primary and secondary aromatic amines via C(sp2)-O bond cleavage is described. The new amination protocol can be applied to a range of substrates bearing diverse functional groups and uses readily available benzophenone imines as an effective nitrogen source.

Rhodium-catalyzed borylation of aryl and alkenyl pivalates through the cleavage of carbonoxygen bonds

Rhodium-catalyzed borylation reactions of aryl and alkenyl pivalates, using a diboron reagent, via the cleavage of carbonoxygen bonds have been developed. The inert nature of the pivalate moiety enables relatively complex aryl boronates to be synthesized via the tandem cross-coupling of carbonhalogen and carbonoxygen bonds.