Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Kabir, Shaila; Iyoda, Masahiko

doi:10.1055/s-2000-8239

Cited by 30 publications

(21 citation statements)

References 18 publications

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“…The synthesis started from the known octamethoxytetraphenylene 1 [4,19–20 29–31], which was demethylated with boron tribromide in CH 2 Cl 2 at −50 °C to room temp. followed by hydrolysis with MeOH (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases

Wuckert

Hägele²,

Gießelmann³

et al. 2009

Beilstein J. Org. Chem.

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SummaryTetraphenylenes 2 with eight peripheral gallic esters were prepared in two steps from octamethoxytetraphenylene 1 in 19–72% yield. Investigation of the mesomorphic properties of 2 by DSC, POM and X-ray diffraction revealed that derivatives 2a–d with short alkoxy chain lengths (C5–C8) did not show any mesomorphic properties, whereas compounds 2e–i with C9–C13 chains displayed rectangular columnar mesophases and compounds 2j–l with C14–C16 chains displayed hexagonal columnar mesophases. Furthermore an anomalous odd-even effect of the clearing points of compounds 2e–l versus chain length was detected.

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Section: Resultsmentioning

confidence: 99%

Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases

Wuckert

Hägele²,

Gießelmann³

et al. 2009

Beilstein J. Org. Chem.

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“…It was prepared in two steps from 2,2′,6,6′-tetrabromobiphenyl, as described by Iyoda and Kabir. 52 At first, tetrabromobiphenyl was lithiated, followed by reaction with zinc(II) bromide to form dibenzozincacyclopentadiene. In a second reaction, 1,8,9,16-tetrabromotetraphenylene (170) was obtained via dimerization involving catalysis with CuCl 2 .…”

Section: Account Syn Lettmentioning

confidence: 99%

Synthesis of Heterocyclic [8]Circulenes and Related Structures

Hensel

Andersen

Plesner

et al. 2015

Synlett

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In this account we give an overview of the synthesis and properties of heterocyclic [8]circulenes. Much of the interest in studying heterocyclic [8]circulenes stems from the planar cyclooctatetraene core often contained in these compounds, which in principle is antiaromatic. We start with a short introduction to the hydrocarbon [n]circulenes and proceed to describe the synthetic chemistry involved in creating tetraoxa[8]circulenes, with particular focus on the acid-mediated oligomerization of benzo-or naphthoquinones, resulting in some simple rules for predicting the outcome of the oligomerization reactions. These rules have guided the synthetic strategies for the preparation of azatrioxa[8]circulenes and diazadioxa[8]circulenes, which will be described in separate sections of this account. More traditional synthetic strategies have been applied in the preparation of octathia[8]circulene, tetrathiatetraselena[8]circulene, and a number of other heterocyclic [8]circulenes, and these synthetic efforts will be highlighted. Finally, a section describing structures that are closely related to the heterocyclic [8]circulenes will be presented, and at the end we will comment on the extensive theoretical work regarding the question of aromaticity/antiaromaticity of the central cyclooctatetraene of heterocyclic[8]circulenes. 1 Introduction 2 Synthesis of [n]circulenes 2.1 [4]Circulene 2.2 [5]Circulene 2.3 [6]Circulene 2.4 [7]Circulene 2.5 [8]Circulene 3 Synthesis of Tetraoxa[8]circulenes: A Historical Perspective 4 Synthesis of Azatrioxa[8]circulenes 5 Synthesis of Diazadioxa[8]circulenes 6 Synthesis of Other Heterocyclic [8]Circulenes 7 Synthesis of Structurally Related Compounds 8 Hetero[8]circulenes and Related Compounds as Tools to Study Aromaticity and Antiaromaticity 9 Conclusion and Outlook

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“…Starting from commercially available 1,3-dibromobenzene (8) we prepared 1-bromobiphenylene (11) according to a modified literature procedure (Scheme 1). [50][51][52][53] The biphenylene 11 forms by Cu II -mediated ring closure of a zinkacyclopentadiene. 53 The latter is accessible in situ by twofold lithiation of 10 and successive transmetallation with ZnBr2.…”

Section: Synthesis Of Biphenylene Ligandsmentioning

confidence: 99%

Non-palindromic (C^C^D) gold(iii) pincer complexes are not accessible by intramolecular oxidative addition of biphenylenes – an experimental and quantum chemical study

Feuerstein

Breher

2021

Dalton Trans.

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Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Cited by 30 publications

References 18 publications

Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases

Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases

Synthesis of Heterocyclic [8]Circulenes and Related Structures

Non-palindromic (C^C^D) gold(iii) pincer complexes are not accessible by intramolecular oxidative addition of biphenylenes – an experimental and quantum chemical study

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