Lewis Acid Promoted Dearomatization of Naphthols

Kulish, Kirill I.; Boldrini, Cosimo; Reis, Marta Castiñeira; Pérez, Juana M.; Harutyunyan, Syuzanna R.

doi:10.1002/chem.202003392

Cited by 9 publications

(2 citation statements)

References 55 publications

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“…In 2020, a two-step dearomative functionalization of β-naphthols promoted by Lewis acids and copper(I) catalyst was disclosed by Harutyunyan’s group (Scheme 3b ). 10 It was possible to achieve dearomative functionalization of naphthol derivatives. However, the products of dearomatization through Lewis acid catalysis were still limited and β-tetralone was often obtained as a result of over-reduction.…”

Section: Construction Of Carbon–hydrogen Bonds At the α-Position Of β...mentioning

confidence: 99%

Dearomatization of α-Unsubstituted β-Naphthols

Xu,

Li,

Feng

et al. 2023

Synlett

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This Account summarizes the highly appealing dearomatization reactions of β-naphthols for the synthesis of highly functionalized, three-dimensional structures starting with simple planar aromatic compounds. The reactions are categorized mainly from the viewpoint of the construction of carbon–hydrogen, carbon–carbon, and carbon–hetero bonds (C–N/O, C–Cl, C–F) at the α-position of β-naphthols. The dearomatized products play an important role in organic synthesis and materials science.1 Introduction2 Construction of Carbon–Hydrogen Bonds at the α-Position of β-Naphthols3 Construction of Carbon–Carbon Bonds at the α-Position of β-Naphthols4 Construction of Carbon–Nitrogen/Oxygen Double Bond at the α-Position of β-Naphthols5 Construction of Carbon–Carbon and Carbon–Oxygen Bonds at the α-Position of β-Naphthols6 Construction of Carbon–Halogen Bonds at the α-Position of β-Naphthols7 Conclusion

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Section: Construction Of Carbon–hydrogen Bonds At the α-Position Of β...mentioning

confidence: 99%

Dearomatization of α-Unsubstituted β-Naphthols

Xu,

Li,

Feng

et al. 2023

Synlett

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“…However, selective dearomatization and functionalization of fused arenes is difficult because harsh conditions are often required to disrupt aromaticity, leading to poor selectivities. As a result, dearomative functionalizations of fused arenes has been largely limited to activated arenes such as indoles [6][7][8][9][10][11][12][13][14][15] and naphthols [16][17][18][19][20] .…”

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confidence: 99%

Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization

Wang

Davies

et al. 2022

Preprint

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Reactions that lead to destruction of aromatic ring systems often require harsh conditions and, thus, take place with poor selectivities. Selective partial dearomatization of fused arenes is even more challenging but it can be a strategic approach to creating versatile, complex polycyclic frameworks. Herein we describe a general organophotoredox approach for the chemo- and regioselective dearomatization of structurally diverse polycyclic aromatics, including quinolines, isoquinolines, quinoxalines, naphthalenes, anthracenes and phenanthrenes. The success of the new method for chemoselective oxidative rupture of aromatic moieties relies on precise manipulation of the electronic nature of the fused polycyclic arenes. Experimental and computational results show that the key to overcoming the intrinsic thermodynamic and kinetic unfavorability of the dearomatization process is an ultimate hydrogen atom transfer (HAT) step, which enables dearomatization to predominate over the otherwise favorable aromatization pathway. We show that this strategy can be applied to rapid synthesis of biologically valued targets and late-stage skeletal remodeling en route to complex structures.

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