Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction

Akın, Esra Turan; Erdoğan, Musa; Daştan, Arif; Saraçoğlu, Nurullah

doi:10.1016/j.tet.2017.07.058

Cited by 18 publications

(5 citation statements)

References 131 publications

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“…: 1 H NMR (400 MHz, CDCl3) δ 8.10 (s, 1H), 7.95 (s, 1H), 7.84-7.77 (m, 1H), 7.7.76-7.67 (m, 1H), 7.59-7.42 (m, 2H), 4.78 (s, 2H).…”

Section: -Bromo-3-(bromomethyl)naphthalene (4)mentioning

confidence: 99%

“…Naphthalene and its derivatives are some of the most functional polycyclic aromatic compounds (PAHs) made up of a large number of aromatic rings [1]. Due to its excellent physicochemical and spectroscopic properties, naphthalene scaffolds found application in various fields of scientific chemistry fields, such as synthetic, materials, medicinal, structural, macromolecular, *Corresponding author: musaerdogan0@gmail.com 1 Kafkas University, Faculty of Engineering and Architecture, Department of Food Engineering, 36100, Kars, Turkey.…”

Section: Introductionmentioning

confidence: 99%

“…Due to its excellent physicochemical and spectroscopic properties, naphthalene scaffolds found application in various fields of scientific chemistry fields, such as synthetic, materials, medicinal, structural, macromolecular, *Corresponding author: musaerdogan0@gmail.com 1 Kafkas University, Faculty of Engineering and Architecture, Department of Food Engineering, 36100, Kars, Turkey. ORCID: https://orcid.org/0000-0001-6097-2862 supramolecular, and fluorescence chemistry; and as backbones or functional devices [1][2][3][4][5]. They have found widespread use as sensors and a marker chromophore unit in biological systems.…”

Section: Introductionmentioning

confidence: 99%

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An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene

Erdoğan

2021

Sakarya University Journal of Science

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Herein, a new efficient method for the synthesis of 2-bromo-3-(bromomethyl)naphthalene is reported. The synthesis is based on (1) preparation of 1,4-dihydronaphthalene via Birch reduction with mild conditions from the reaction of naphthalene, and (2) the reaction between 1,4-dihydronaphthalene and dichlorocarbene formed in situ from chloroform and potassium tert-butoxide (t-BuOK), and (3) access to the key intermediate 1H-cyclopropa[b]naphthalene from the reaction of 1,1-dichloro-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene with t-BuOK, followed by ring-opening of the cyclopropane via bromination with molecular bromine (Br2). This synthetic sequence allows simple preparation of 2-bromo-3-(bromomethyl)naphthalene in higher yields compared to the two previously reported syntheses. The synthetic approach is modular, low cost, and rapid, and can be utilized to synthesize building blocks of naphthalene derivatives.

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“…: 1 H NMR (400 MHz, CDCl3) δ 8.10 (s, 1H), 7.95 (s, 1H), 7.84-7.77 (m, 1H), 7.7.76-7.67 (m, 1H), 7.59-7.42 (m, 2H), 4.78 (s, 2H).…”

Section: -Bromo-3-(bromomethyl)naphthalene (4)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene

Erdoğan

2021

Sakarya University Journal of Science

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“…The Diels-Alder (DA) reaction represents a powerful and versatile synthetic tool to build simple and complex molecules, forming cyclic, bicyclic or tricyclic products via the formation of two new single CÀ C bonds. [1][2][3][4][5] In addition, DA is considered one of the most important reactions in organic chemistry due to its high level regio and stereoselectivity, [6][7][8] which usually requires electron-withdrawing groups (EWG) in the dienophile and electron-rich dienes, or vice versa, to afford acceptable reaction rates. [9] The mechanism of the DA reaction proceeds in a concerted way (one transition state, TS) and can be classified as synchronous or asynchronous depending on whether the new CÀ C bonds are or are not formed in unison.…”

Section: Introductionmentioning

confidence: 99%

Diels‐Alder Reactivity of a Chiral Anthracene Template with Symmetrical and Unsymmetrical Dienophiles: A DFT Study

2020

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In this work, we used Density Functional Theory calculations to assess the factors that control the reactivity of a chiral anthracene template with three sets of dienophiles including maleic anhydrides, maleimides and acetoxy lactones in the context of Diels‐Alder cycloadditions. The results obtained here (at the M06‐2X/6‐311++G( d,p ) level of theory) suggest that the activation energies for maleic anhydrides and acetoxy lactones are dependent on the nature of the substituent in the dienophile. Among all studied substituents, only −CN reduces the energy barrier of the cycloaddition. For maleimides, the activation energies are independent of the heteroatom of the dienophile and the R group attached to it. The analysis of frontier molecular orbitals, charge transfer and the activation strain model (at the M06‐2X/TZVP level based on M06‐2X/6‐311++G( d,p ) geometries) suggest that the activation energies in maleic anhydrides are mainly controlled by the amount of charge transfer from the diene to the dienophile during cycloaddition. For maleimides, there is a dual control of interaction and strain energies on the activation energies, whereas for the acetoxy lactones the activation energies seem to be controlled by the degree of template distortion at the transition state. Finally, calculations show that considering a catalyst on the studied cycloadditions changes the reaction mechanism from concerted to stepwise and proceed with much lower activation energies.

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“…In 2016, Kubozono and co-workers reported the PAHs of a repeating W-shaped pattern by a repetition of Wittig reactions followed by photocyclization . In 2014, Greaney prepared trinaphthylene using 2-bromoaryl boronic ester by metal-catalyzed benzyne cyclotrimerization and in 2017, Dastan also reported the synthesis of trinaphthylene using benzobarrelene–bromostannylalkene by cyclotrimerization and Diels–Alder reaction . However, the intrinsic difficulties in preparing substrates and tedious processes to prepare the precursors of PAHs are major drawbacks for their further development and applications.…”

mentioning

confidence: 99%

Synthesis of Polycyclic Aromatic Hydrocarbons (PAHs) via a Transient Directing Group

Tang

Wang

et al. 2018

Org. Lett.

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In this work, an efficient synthetic route was developed to construct PAHs with diverse shape, width, and edge topology. The precursors of PAHs were obtained by using a direct arylation of arenes via a transient ligand-directed C−H functionalization strategy and the cycloaromatization was readily achieved by using a Brønsted acid catalyst. This novel route provides an opportunity to build up PAHs in a highly efficient manner.

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Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction

Cited by 18 publications

References 131 publications

An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene

An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene

Diels‐Alder Reactivity of a Chiral Anthracene Template with Symmetrical and Unsymmetrical Dienophiles: A DFT Study

Synthesis of Polycyclic Aromatic Hydrocarbons (PAHs) via a Transient Directing Group

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