Visual detection of formaldehyde by highly selective fluorophore labeling via gold(<scp>iii</scp>) complex-mediated three-component coupling reaction

Wong, Kong-Fan; Deng, Jie‐Ren; Wei, Xiaoqun; Shao, Shi-Ping; Xiang, Da-Peng; Wong, Man Leung

doi:10.1039/c5ob00966a

Cited by 19 publications

(10 citation statements)

References 27 publications

(2 reference statements)

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“…We decided to test several other procedures involving coupling reagents (Table ). The reactions with N‐( 3‐dimethylaminopropyl)‐ N ′‐ethylcarbodiimide hydrochloride (EDC), N , N , N′ , N′ ‐tetramethyl‐ O ‐(1 H ‐benzotriazol‐1‐yl)uronium hexafluorophosphate (HBTU), and N ‐ethoxycarbonyl‐2‐ethoxy‐1,2‐dihydroquinoline (EEDQ) as coupling agents failed to improve the reaction output . Finally, we decided to adopt the procedure of Ulven and co‐workers; the use of chlorodipyrrolidinocarbenium hexafluorophosphate (PyClU) as the coupling reagent allowed us to isolate CoumDimer .…”

Section: Resultssupporting

confidence: 53%

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

Kielesiński

Morawski

Sobolewski

et al. 2017

Chemistry A European J

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The synthesis of a weakly coupled, strongly polarized coumarin dimer has been achieved for the first time. The three-step strategy comprises the Skattebøl formylation followed by the Knoevenagel reaction and the formation of a tertiary amide by using a peptide-type procedure. The molecule consists of two different coumarin moieties: One is a classical donor-acceptor system and the second one possesses a weaker amide donor at the 7-position. The polarized coumarin dimer can form an electronically conjugated structure possessing an electric dipole larger than that of 7-(dimethylamino)coumarin-3-carboxylic acid. The limited flexibility of the inter-coumarin connection results in stable conformers of different electric dipole moments and complex photophysics. In the solid state, this compound has a strongly bent conformation with the two coumarin units forming an angle of around 74°. In solution, two conformers are in equilibrium. The existence of the molecule as two conformers in the ground state has been confirmed by optical studies, and further corroborated by molecular calculations. The fluorescence spectra possess a unique feature: A charge-transfer band (ca. 550 nm) is visible only in nonpolar or weakly polar solvents. Optical spectroscopy studies coupled with molecular calculations allowed us to rationalize this phenomenon: The large amplitude of intramolecular motions is responsible for the conformational isomerization as well as producing a conical intersection between the potential energy surfaces of the excited singlet state and the ground state, which opens an internal conversion channel that effectively competes with the fluorescence of the conformers.

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Section: Resultssupporting

confidence: 53%

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

Kielesiński

Morawski

Sobolewski

et al. 2017

Chemistry A European J

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“…In the past few years, we have reported gold(III)‐catalyzed three‐component coupling reactions with different aldehydes, including aldehyde‐containing oligosaccharides . We have demonstrated the application of A 3 ‐coupling reaction for visual detection of formaldehyde in food . In view of the versatility of the multicomponent A 3 ‐coupling reactions, it is worthy of exploring the application of the gold(III)‐catalyzed three‐component coupling reaction for the fluorescent labelling of glycans.…”

Section: Methodsmentioning

confidence: 99%

“…Based on the above experimental results, we have optimized our reaction conditions that the conversion of the gold(III)‐mediated three‐component coupling reaction would be the highest when using KAuCl 4 as the catalyst and DCE/H 2 O (5 : 1) as the reaction medium. In line with our previous studies on the reaction temperature optimization of the gold(III)‐mediated three‐component coupling reaction, the reaction temperature of 50 °C was chosen.…”

Section: Methodsmentioning

confidence: 99%

“…[22] We have demonstrated the application of A 3 -coupling reaction for visual detection of formaldehyde in food. [23] In view of the versatility of the multicomponent A 3coupling reactions, [24] it is worthy of exploring the application of the gold(III)-catalyzed three-component coupling reaction for the fluorescent labelling of glycans.…”

Section: Fluorescent Labelling Of Glycans With Fret-based Probes In Amentioning

confidence: 99%

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Fluorescent Labelling of Glycans with FRET‐Based Probes in a Gold(III)‐Mediated Three‐Component Coupling Reaction

et al. 2019

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Single‐site multifunctionalization of glycans is of importance in biological studies considering its crucial role in mediating biological events and human diseases. In this paper, a novel approach for multifunctional labelling of glycans has been developed featuring the use of fluorescence resonance energy transfer‐based (FRET‐based) probes for fluorescent labelling of glycans through a gold(III)‐mediated three‐component coupling reaction. Oxidation of glycans into aldehydes followed by the A3‐coupling reaction with FRET‐based probes resulted in the single‐site formation of fluorescent propargylamine products. The conversion of labelled glycans can be revealed by ratiometric analysis of the FRET signals. This labelling approach results in multifunctionalization of glycans with high selectivity and conversion between 66 and 69 %.

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“…However, to the best of our knowledge, the formation of propargylamides via the coupling of amides, aldehydes and alkynes has never been reported before. 13 Coinage transition-metal catalysts, such as gold, have shown excellent activity for the A 3 -coupling, 14 and have been highly effective for the cyclization of acetylenic compounds. 15 Thus, we envisioned that a judicious choice of gold catalyst might effectively catalyze both the A 3 -coupling and the tandem cyclization steps, providing access to highly functionalized oxazoles in a single pot.…”

Section: Introductionmentioning

confidence: 99%

Gold-catalyzed tandem reactions of amide–aldehyde–alkyne coupling and cyclization-synthesis of 2,4,5-trisubstituted oxazoles

et al. 2015

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Visual detection of formaldehyde by highly selective fluorophore labeling via gold(iii) complex-mediated three-component coupling reaction

Abstract: A novel method for visual detection of formaldehyde with excellent selectivity via a gold(iii) complex-mediated three-component coupling reaction of resin-linked sterically bulky amines and fluorescent alkynes has been developed.

Cited by 19 publications

References 27 publications

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

Fluorescent Labelling of Glycans with FRET‐Based Probes in a Gold(III)‐Mediated Three‐Component Coupling Reaction

Gold-catalyzed tandem reactions of amide–aldehyde–alkyne coupling and cyclization-synthesis of 2,4,5-trisubstituted oxazoles

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