Synthesis and Characterization of (Di)Benzosilaphenalenes

Tokoro, Yuichiro; Ōyama, Toshiyuki

doi:10.1246/cl.170939

Cited by 11 publications

(3 citation statements)

References 30 publications

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“…However, the reactions of naphthols at the peri ‐position have been limited to phenylation at high temperatures and a series of alkynylations,, while the reactions of naphthylamines at the peri ‐position have required picolinamide as the directing group and lead to the installation of a limited set of groups ,,–,–. In other cases, reactions of 1‐naphthol and 1‐aminonaphthalene derivatives have formed annulated products in which the directing groups (OH and NR) are linked to the newly installed functionalities (Scheme b) –,,. In such structures, manipulations of the directing group and the newly introduced functional groups are difficult.…”

Section: Methodsmentioning

confidence: 99%

Iridium‐Catalyzed, Silyl‐Directed, peri‐Borylation of C−H Bonds in Fused Polycyclic Arenes and Heteroarenes

Hartwig

2018

Angewandte Chemie

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peri‐Disubstituted naphthalenes exhibit interesting physical properties and unique chemical reactivity, due to the parallel arrangement of the bonds to the two peri‐disposed substituents. Regioselective installation of a functional group at the position peri to 1‐substituted naphthalenes is challenging due to the steric interaction between the existing substituent and the position at which the second one would be installed. We report an iridium‐catalyzed borylation of the C−H bond peri to a silyl group in naphthalenes and analogous polyaromatic hydrocarbons. The reaction occurs under mild conditions with wide functional group tolerance. The silyl group and the boryl group in the resulting products are precursors to a range of functional groups bound to the naphthalene ring through C−C, C−O, C−N, C−Br and C−Cl bonds.

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Section: Methodsmentioning

confidence: 99%

Iridium‐Catalyzed, Silyl‐Directed, peri‐Borylation of C−H Bonds in Fused Polycyclic Arenes and Heteroarenes

Hartwig

2018

Angewandte Chemie

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“…In addition, sulfur-containing aromatic architectures could also be obtained after oxidation of the thioether moiety into sulfoxides followed by cyclization under acidic conditions. 65 Recently Yu and Che, designed an effective Rh I -catalyzed C-H arylation of tertiary phosphines providing a route to peri-substituted (naphthalen-1-yl)phosphines in moderate to high yields (Scheme 15). 66 In the proposed mechanism, the naphthalene phosphane is assumed to play both the role of ligand and substrate.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

C–H Functionalization Strategies in the Naphthalene Series: Site Selections and Functional Diversity

Large

Prim²

2020

Synthesis

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Naphthalene is certainly not a common arene. In contrast to benzene, the bicyclic feature of naphthalene offers multiple differentiable positions and thus a broad diversity of substitution patterns. Naphthalene is a central building block for the construction of elaborated polycyclic architectures with applications in broad domains such as life and materials sciences. As a result, C–H functionalization strategies specially designed for naphthalene substrates have become essential to install valuable substituents on one or both rings towards polysubstituted naphthalenes. This short review provides a focus on uncommon substitution patterns; however, classical ortho C–H activation is not covered.1 Introduction2 C–H Functionalization Using a Directing Group Located at Position 12.1 Functionalization on the Ring Bearing the DG: 1,3-Substitution Pattern2.2 Functionalization on the Ring Bearing the DG: 1,4-Substitution Pattern2.3 Functionalization on the Neighboring Ring: 1,6-, 1,7- and 1,8-Substitution Patterns3 C–H Functionalization Using a Directing Group Located at Position 23.1 Functionalization on the Ring Bearing the DG: 2,4- and 2,1-Substitution Patterns3.2 Miscellaneous Substitution Patterns4 Bis C–H Functionalization4.1 Symmetrical Bisfunctionalization: 1,2,8-Substitution Pattern4.2 Symmetrical Bisfunctionalization: 2,3,1-Substitution Pattern4.2 Unsymmetrical Bisfunctionalization: 2,3,1-Substitution Pattern4.3 Symmetrical Bisfunctionalization: 2,4,8-Substitution Pattern5 Conclusion and Outlook

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“…Recently, we have developed ruthenium-catalyzed annulation of hydrosilylanthracenes with internal alkynes through Si–H and C–H bonds cleavage. 7 The catalytic cycle of the annulation probably involves a five-membered ruthenacycle composed of ruthenium, silicon and three carbons from the anthracene moiety. Insertion of alkynes into the ruthenacycles followed by reductive elimination affords the annulation products.…”

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confidence: 99%

Intra- and intermolecular interaction of anthracene moieties in 7,8-disilabicyclo[3.3.0]octadienyl-bridged bisanthracenes

et al. 2018

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Synthesis and Characterization of (Di)Benzosilaphenalenes

Cited by 11 publications

References 30 publications

Iridium‐Catalyzed, Silyl‐Directed, peri‐Borylation of C−H Bonds in Fused Polycyclic Arenes and Heteroarenes

Iridium‐Catalyzed, Silyl‐Directed, peri‐Borylation of C−H Bonds in Fused Polycyclic Arenes and Heteroarenes

C–H Functionalization Strategies in the Naphthalene Series: Site Selections and Functional Diversity

Intra- and intermolecular interaction of anthracene moieties in 7,8-disilabicyclo[3.3.0]octadienyl-bridged bisanthracenes

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