Oxidative coupling aerobic

There are no reports of chiral complex catalysts that could catalyze the aerobic oxidative coupling of 2-naphthol at a reasonable reaction rate with high enantioselectivity. The reactions mentioned above are accomplished in 24 h or in 7-10 days. These drawbacks should be overcome in the near future. 

As can be seen in the scheme below, a series of substituted 2-(2-aminothiazol-4-yl)-benzo[ ]furans with inhibitory activity for leukotriene B4 were made from benzofurans via acylation, followed by Hantzsch thiazole formation <070BC3083>. 2-Substituted benzo[ ]furans could also be generated via an aerobic oxidative coupling of 2-unsubstituted benzo[ ]furans with arenes through the palladium-catalyzed double C-H activation <07OL3137>. In addition, 2,3-diarylbenzo h I uran could be constructed by a palladium-catalyzed arylation of benzo[6]furan with an aryl chloride in the presence of a bulky, and electron-rich phosphine <07OL1449>. 

Dwight TA, Rue NR, Charyk D, Josselyn R, DeBoef B (2007) C-C bond formation via double C-H functionalization aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls. Org Lett 9 3137-3139... 

The following reference describes a Cu-catalyzed aerobic oxidative coupling reaction Mudryk, B., Zheng, B., Chen, K., and Eastgate, M.D. (2014) Org. Process Res. Dev., 18, 520-527. 

Pd-catalyzed aerobic oxidative coupling of arenes provides efficient access to biaryl compounds. The reaction exhibits near-ideal atom economy with water as the sole by-product however, it typically suffers from low regioselectivity and the blaryl products are often susceptible to further oxidation to afford oligomers. 

Scheme 8.5 Pd-catalyzed aerobic oxidative coupling of dimethyl phthalate.

DeBoef, B. Aerobic oxidative coupling for the formation biaryls. W02008067443, 6 5... 

Scheme 9.18 Enantioselective and aerobic oxidative coupling of 2-naphthol derivatives using a chiral dinuclear vanadium(v) complex in water, reported by Sasai and Takizawa. - ...

The mechanism (Scheme 3) of a Cu-catalysed aerobic oxidative coupling reaction of A-phenyl tetrahydroisoquinoline (15) with isopropenyloxy(trimethyl)silane (16)... 

Noji, M., Nakajima, M., and Koga, K., A new catalytic system for aerobic oxidative coupling of 2-naphthol derivatives by the use of CuCl-amine complex a practical synthesis of binaphthol derivatives. Tetrahedron Lett., 7983 (1994). 

Donthiri RR, Patil RD, Adimurthy S et al (2012) NaOH-catalyzed imine synthesis aerobic oxidative coupling of alcohols and amines. Eur J Org Chem 24 4457- 1460... 

The effect of amine ligands in copper(I)-catalyzed chemose-lective amide carbamoylation has been studied. Catalytic asymmetric synthesis of binaphthol derivatives is also reported by aerobic oxidative coupling of 3-hydroxy-2-naphthoates with chiral diamine-copper complexes (eq 15). ... 

Kegnaes S, Mielby J, Mentzel UV, Jensen T, Fristrup P, Riisager A (2012) One-pot synthesis of amides by aerobic oxidative coupling of alcohols or aldehydes with amines using supported gold and base as catalysts. Chem Commun 48(18) 2427-2429... 

It is only very recently that rhodium-based catalytic systems have been described in efficient oxidative olefination reactions. Inspired by the work of Satoh and Miura on rhodium/copper-catalyzed aerobic oxidative coupling of benzoic acids with internal allqmes or acrylates (Scheme 9.11), Glorius and co-workers described, in 2012, a rhodium-catalyzed directing group assisted olefination of 2-aryloxazolines under air. This method, which necessitated rhodium, silver and copper metal sources, afforded the desired olefin-oxazoline products in moderate-to-good yields (Scheme 9.12). 

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