- Palladium-Catalyzed C8-Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton
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Herein, a direct C8-oxygenation of naphthalene derivatives is described. Different carbonyl groups were used as directing group to deliver corresponding naphthols via a palladium-catalyzed oxidation reaction using PhI(OAc)2 in a TFA/TFAA mixture. Interestingly, when Weinreb amide was employed as the directing group, the naphtholactone skeleton was directly obtained. This methodology was applied to the synthesis of variously substituted naphtholactones. (Figure presented.).
- Berrou, Caroline,Prévost, Sébastien
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p. 4091 - 4095
(2021/07/19)
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- Pd(OAc)2-catalyzed oxidative carbonylation of aromatics: Synthesis of naphthalenecarboxylic acids
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The liquid-phase oxidative carbonylation of aromatics leading to aromatic carboxylic acids is studied to develop new approaches to 2,6- naphthalenedicarboxylic acid (NDA) preparation. It is shown that the catalytic system Pd(OAc)2/K2S2O8 allows the synthesis of naphthalic anhydride (NAn) by direct oxidative carbonylation of naphthalene under mild conditions (25 C, 2 atm CO). The subsequent alkaline hydrolysis of NAn and isomerization of the obtained 1,8-naphthalenedicarboxylic acid salt is known to lead to NDA.
- Elman, Alexander R.
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p. 5527 - 5531
(2013/09/23)
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- A missing relative: A Hoveyda-Grubbs metathesis catalyst bearing a peri-substituted naphthalene framework
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Molecular scaffolds of polycyclic aromatic hydrocarbons can serve as unique tools to control the molecular and electronic structure of coordination compounds. Herein, we report the synthesis and properties of a Hoveyda-Grubbs metathesis catalyst bearing a chelating benzylidene ligand assembled on peri-substituted naphthalene. In contrast to other reported naphthalene-based complexes (Barbasiewicz, M. and Grela, K.Chem. Eur. J. 2008, 14, 9330-9337), it exhibits a very fast initiation behavior, attributed to a distorted molecular structure and reduced π-electron delocalization within the chelate ring.
- Barbasiewicz, Michal,Grudzien, Krzysztof,Malinska, Maura
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p. 3171 - 3177
(2012/06/04)
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- Selective synthesis of meso-naphthylporphyrins
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A series of novel meso-(8-substituted naphth-1-yl)porphyrins has been synthesized creating derivatives with a tight recognition environment above the porphyrin plane. The selective synthesis of single atropisomers is discussed. Condensation of bisnaphthaldehyde 12 with phenyldipyrromethane unexpectedly led to selective synthesis of the α,α-5,10-bridged isomer 14. A mechanism is proposed for this unusual scrambling, and alternative syntheses of α,α-5,15-bisnaphthylporphyrins are described. Synthesis of 5,15-analogues can be achieved by employing (pentafluorophenyl)-dipyrromethane or via presynthesis of a bis(dipyrromethane) derivative 22 (from bisnaphthaldehyde 12) and subsequent condensation with benzaldehyde.
- Cammidge, Andrew N.,Oeztuerk, Orhan
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p. 7457 - 7464
(2007/10/03)
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- CHEMISTRY OF 1,8-SUBSTITUTED NAPHTHALENES. XIX. SYNTHESIS OF N-SUBSTITUTED 2-AMINONAPHTHOFURYLIUM SALTS
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N-Substituted 2-aminonaphthofurylium salts were obtained by heating 8-hydroxy-1-naphthamides with phosphorus oxychloride, whereas the lactone of 8-hydroxy-1-naphthoic acid (naphtholactone) was obtained by heating in trifluoroacetic acid.With phosphorus oxychloride the amide unsubstituted at the nitrogen gives 8-hydroxy-1-naphthonitrile.In organic solvents the synthesized salts react with water and give naphtholactone or open to 8-hydroxy-1-naphthamides, depending on the concentration.The corresponding imino bases were obtained by the deprotonation of the mono-N-substituted salts.
- Pikus, A. L.,Mezheritskii, V. V.
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p. 150 - 154
(2007/10/02)
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