108972-06-1

Upstream product

• 108979-87-9 4-p-tolylnaphthalen-1-ol 
• 5720-05-8 4-methylphenylboronic acid 
• 524-42-5 1,2-naphthoquinone 
• 227954-71-4 4-(4-methylphenyl)-2-naphthol 

Downstream Products

• 76103-24-7 4-(p-tolyl)coumarin 

Relevant academic research and scientific papers

Rapid, Operationally Simple, and Metal-free NBS Mediated One-pot Synthesis of 1,2-Naphthoquinone from 2-Naphthol

A metal-free, one-pot synthesis of 1,2-naphthoquinone was accomplished from 2-naphthol by utilizing economically cheap NBS under open air conditions. Initial formation of 1,1-dibromonaphthalen-2-one and subsequent transformation afforded the 1,2-naphthoquinone. This oxidation was completed within 30 min and had broad substrate scope. Moreover, this system tolerated heterocyclic systems and was also applicable to 1,3-dicarbonyl systems. This practical approach with short reaction times, a simple workup, and insensitivity to moisture could override the usage of expensive and hazardous oxidizing and metal reagents. (Figure presented.).

Rhodium(I)-Catalyzed Decarbonylative Aerobic Oxidation of Cyclic α-Diketones: A Regioselective Single Carbon Extrusion Strategy

A rhodium-catalyzed decarbonylative aerobic oxidation of cyclic α-diketones has been developed for the first time, where the regioselective formations of α-pyrones and isocoumarins have been achieved. The current decarbonylative aerobic oxidation pathway proceeds via the C-C bond cleavage followed by a C-O bond formation, representing a biomimetic oxidation approach to unsaturated six-membered cyclic lactones. The unique ability of rhodium catalysts to induce the decarbonylative aerobic oxidation opens up a new synthetic toolbox that utilizes the "regioselective single carbon" extrusion strategy.

Copper-catalyzed divergent oxidative pathways of 2-naphthol derivatives:: Ortho -naphthoquinones versus 2-BINOLs

Catalyst-dependent divergent pathways of 2-naphthol derivatives have been investigated. A readily available CuCl2-DMAP catalyst system promotes the aerobic oxidation of 2-naphthol derivatives to ortho-naphthoquinones whereas switching the catalyst system to Cu(OAc)2-DBN under an argon atmosphere allows the oxidative coupling of 2-naphthols to 1,1′-bi-2-naphthols (BINOLs) in good to excellent yields.

Practical C-H functionalization of quinones with boronic acids

A direct functionalization of a variety of quinones with several boronic acids has been developed. This scalable reaction proceeds readily at room temperature in an open flask using inexpensive reagents: catalytic silver(I) nitrate in the presence of a persulfate co-oxidant. The scope with respect to quinones is broad, with a variety of alkyl- and arylboronic acids undergoing efficient cross-coupling. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone. This method has been applied to complex substrates, including a steroid derivative and a farnesyl natural product.