An Efficient Ag+-Selective Fluorescent Chemosensor Derived from Tribenzotriquinacene

Li, Zhimin; Hu, Da; Wei, Junfa; Qi, Qiuli; Cao, Xiao‐Ping; Chow, Hak‐Fun; Kuck, Dietmar

doi:10.1055/s-0036-1591759

Synthesis

2018

DOI: 10.1055/s-0036-1591759

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An Efficient Ag+-Selective Fluorescent Chemosensor Derived from Tribenzotriquinacene

Zhimin Li¹,

Da Hu²,

Junfa Wei³

et al.

Abstract: A new C 3v -symmetrical tribenzotriquinacene (TBTQ) derivative bearing six 8-quinolinyloxymethyl units at the rim of the bowl-shaped molecular framework is synthesized in a single-step by six-fold etherification of the corresponding hexakis(chloromethyl)-TBTQ precursor with 8-hydroxyquinoline. The resulting compound acts as a fluorescence chemosensor, producing a ‘turn-off’ fluorescent quenching response in the presence of Ag+ ions, and is highly selective toward Ag+ over other cations,… Show more

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Cited by 28 publications

References 12 publications

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C5‐Disubstituted Meldrum's Acid Derivatives as Platform for the Organocatalytic Synthesis of C3‐Alkylated Dihydrocoumarins

Martzel

Annibaletto

Levacher³

et al. 2019

Adv Synth Catal

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C5-disubstituted Meldrum's acid precursors were shown to be a useful platform for the synthesis of an array of 3-alkylated dihydrocoumarins with up to 93:7 er, thanks to an enantioselective domino cyclization-decarboxylative-protonation reaction triggered by an unprecedented benzhydrylderived cupreine organocatalyst. This cyclization sequence was extended to an emerging organocatalytic decarboxylative-chlorination reaction in the presence of trichloroquinolinone and by means of a bifunctional cinchona derived Brønsted base which gave rise to the formation of dihydrocoumarins (up to 79:21 er) with a tertiary chlorinated stereocenter.Amongst the privileged coumarin scaffolds in medicinal chemistry, the dihydrocoumarin derivatives are widely distributed within naturally occurring molecules and bioactive compounds. [1] Consequently, several groups have developed catalytic enantioselective syntheses of 3,4-disubstituted chroman-2-ones [2] and, to a much lesser extent, 3,3-disubstituted homologues (Scheme 1). [3] Nevertheless, the construction of enantioenriched 3-substituted derivatives turned out to be more challenging. To the best of our knowledge, the group of Scheidt has reported the single one-step asymmetric construction of 3-substituted dihydrocoumarins upon NHC organocatalysis eliciting a (4 + 2) cycloaddition reaction with er ranging from 75:25 to 93:7. [4] Beside the elegant but two steps enamine-based approaches developed by Xie and Liu, [5a-e] requiring the final oxidation of a lactol intermediate, List and co-workers have pioneered the challenging enantiose-lective delivery of a small proton atom to ketene dithioacetals. [5f] One of the obtained product was hydrolyzed into an a-phenyl dihydrocoumarin with high enantiomeric excess. In view of this background, an expedious synthetic sequence furnishing C3-substituted dihydrocoumarin remains desirable.Very recently, the group of Guiry achieved the synthesis of a series of 3-aryl dihydrocoumarins with er ranging from 65:35 to 94:6 (Scheme 1b). [6] This functionalization strategy takes advantage of the palladium-catalyzed decarboxylative protonation reaction [7] in the presence of ephedrine as a chiral stoichiometric source of proton. Although several teams ventured into this convenient enantioselective protonation (EP) strategy, mostly from hemimalonic esters in organocatalysis, only the groups of Brunner, Rouden, Zhang and Song succeeded in getting good er (rarely > 95:5) albeit at the expense of the use of high catalyst loading (up to 1 equiv.). [8,9] Scheme 1.

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C5‐Disubstituted Meldrum's Acid Derivatives as Platform for the Organocatalytic Synthesis of C3‐Alkylated Dihydrocoumarins

Martzel

Annibaletto

Levacher³

et al. 2019

Adv Synth Catal

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An Efficient Chan–Lam S‐Arylation of Arylthioureas with Arylboronic Acids

et al. 2018

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A convenient and efficient protocol has been developed for the preparation of aryl‐isothioureas based on the Chan–Lam C–S coupling reaction. The desired aryl‐isothioureas were synthesized in good yields (up to 95 %) in the presence of Cu(OAc)2·H2O as catalyst and bipyridine as ligand. A variety of functional groups on the aryl‐thiourea and arylboronic acid reagents are tolerated. The method features mild reaction conditions and good yields, thereby illustrating its practical synthetic value in organic synthesis.

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Copper(II)‐Promoted Cascade Synthesis of 2‐Aminobenzothiazoles Starting from 2‐Iodoanilines and Sodium Dithiocarbamates

et al. 2018

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A facile and efficient formation of 2‐aminobenzothiazoles by a copper(II)‐promoted one‐pot cascade process was developed. The desired 2‐aminobenzothiazoles were synthesized in good to excellent yields (up to 97 %) in the presence of Cu(OAc)2 and K2CO3, a variety of functional groups on 2‐iodoanilines could be tolerated. The method features ligand‐free and mild reaction conditions and good yields, illustrating its practical synthetic value in some potentially biologically active compounds.

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An Efficient Ag+-Selective Fluorescent Chemosensor Derived from Tribenzotriquinacene

Cited by 28 publications

References 12 publications

C5‐Disubstituted Meldrum's Acid Derivatives as Platform for the Organocatalytic Synthesis of C3‐Alkylated Dihydrocoumarins

C5‐Disubstituted Meldrum's Acid Derivatives as Platform for the Organocatalytic Synthesis of C3‐Alkylated Dihydrocoumarins

An Efficient Chan–Lam S‐Arylation of Arylthioureas with Arylboronic Acids

Copper(II)‐Promoted Cascade Synthesis of 2‐Aminobenzothiazoles Starting from 2‐Iodoanilines and Sodium Dithiocarbamates

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