Push–pull chromophores by reaction of 2,3,5,6-tetrahalo-1,4-benzoquinones with 4-(N,N-dialkylanilino)acetylenes

Dengiz, Çağatay; Prange, C.; Gaweł, Przemysław; Trapp, Nils; Boudon, Corinne; Diederich, François

doi:10.1016/j.tet.2016.01.017

Cited by 18 publications

(17 citation statements)

References 89 publications

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“…The reacting bonds in entries 9a nd 10 are colored. [44] Thefirst reaction in ac ascade of reactions is the [2+ +2] CA,s imilar to that of DDQ.I nc ontrast, chloranil (22) This thermal rearrangement proceeds through biradical intermediates.…”

Section: Reactivity Of Halo-p-benzoquinonesmentioning

confidence: 99%

“…[43] 2,3,5,6-Tetrahalo-1,4-quinones afforded different types of final products.T etrafluoroquinone 20 reacted with two equivalents of 15 upon heating in 1,2-dichloroethane to afford (AE)-21 in 20 %yield. [44] Thefirst reaction in ac ascade of reactions is the [2+ +2] CA,s imilar to that of DDQ.I nc ontrast, chloranil (22)…”

Section: Reactivity Of Halo-p-benzoquinonesmentioning

confidence: 99%

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The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

2018

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The [2+2] cycloaddition-retroelectrocyclization (CA-RE) reaction between electron-rich alkynes and electron-deficient alkenes is an efficient procedure to create nonplanar donor-acceptor (D-A) chromophores in both molecular and polymeric platforms. They feature attractive properties including intramolecular charge-transfer (ICT) bands, nonlinear optical properties, and redox activities for use in next-generation electronic and optoelectronic devices. This Review summarizes the development of the CA-RE reaction, starting from the initial reports with organometallic compounds to the extension to purely organic systems. The structural requirements for rapid, high-yielding transformations with true click chemistry character are illustrated by examples that include the broad alkyne and alkene substitution modes. The CA-RE click reaction has been successfully applied to polymer synthesis, with the resulting polymeric push-pull chromophores finding many interesting applications.

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Section: Reactivity Of Halo-p-benzoquinonesmentioning

confidence: 99%

Section: Reactivity Of Halo-p-benzoquinonesmentioning

confidence: 99%

The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

2018

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“…In 2016, tetrasubstituted fluoroalkenes were obtained by Diederich and co-workers from the reaction of 2,3,5,6tetrafluoro-p-benzoquinone, a fluorinated analogue of DDQ, and N,N-dialkyl-4-ethynylanilines (Scheme 252). 231 The formation of the final products is proposed to involve a [2+2] cycloaddition reaction with one equivalent of the alkyne as well as the conjugated addition of another equivalent.…”

Section: Allylic Substitution Reactionsmentioning

confidence: 99%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

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“…Das Tetrafluorchinon 20 ergab beim Erhitzen mit 15 (2 Äquiv.) in 1,2‐Dichlorethan das Produkt (±)‐ 21 . Die erste in einer Kaskade von Reaktionen ist die [2+2]‐CA‐Reaktion, ähnlich wie bei der Umsetzung mit DDQ.…”

Section: Molekulare Nichtplanare Push‐pull‐chromophore üBer Die Ca‐runclassified

Die [2+2]‐Cycloadditions‐Retroelektrocyclisierungs(CA‐RE)‐Klick‐Reaktion: ein einfacher Zugang zu molekularen und polymeren Push‐pull‐Chromophoren

Michinobu

Diederich

2018

Angewandte Chemie

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Die [2+2]‐Cycloadditions‐Retroelektrocyclisierungs(CA‐RE)‐Reaktion von elektronenreichen Alkinen mit elektronenarmen Alkenen ist ein effizientes Verfahren zur Bildung nichtplanarer Donor‐Akzeptor‐Chromophore sowohl in molekularen als auch in polymeren Plattformen. Diese Chromophore zeigen ansprechende Eigenschaften, wie intramolekulare Charge‐Transfer(ICT)‐Banden, nichtlineare optische Eigenschaften und Redox‐Eigenschaften zur Verwendung in elektronischen und optoelektronischen Funktionseinheiten der nächsten Generation. Dieser Aufsatz fasst die Entwicklung der CA‐RE‐Reaktion zusammen, beginnend mit den anfänglichen Berichten über Organometallverbindungen bis hin zu rein organischen Systemen. Die strukturellen Voraussetzungen für schnelle Umsetzungen in hohen Ausbeuten, Merkmale echter Klick‐Chemie, werden anhand von Beispielen dargelegt, die die breiten möglichen Alkin‐ und Alkensubstitutionsmuster belegen. Die CA‐RE‐Klick‐Reaktion wurde erfolgreich in der Polymerchemie eingesetzt. Die gebildeten polymeren Push‐pull‐Chromophore finden dabei zahlreiche interessante Anwendungen.

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Push–pull chromophores by reaction of 2,3,5,6-tetrahalo-1,4-benzoquinones with 4-(N,N-dialkylanilino)acetylenes

Cited by 18 publications

References 89 publications

The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

The [2+2] Cycloaddition‐Retroelectrocyclization (CA‐RE) Click Reaction: Facile Access to Molecular and Polymeric Push‐Pull Chromophores

Synthesis of Monofluoroalkenes: A Leap Forward

Die [2+2]‐Cycloadditions‐Retroelektrocyclisierungs(CA‐RE)‐Klick‐Reaktion: ein einfacher Zugang zu molekularen und polymeren Push‐pull‐Chromophoren

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