Convenient Access to Carbohydrate–BODIPY Hybrids by Two Complementary Methods Involving One‐Pot Assembly of “Clickable” BODIPY Dyes

Martinez-Gonzalez, Mayra R.; Urías‐Benavides, Arlette; Alvarado-Martínez, Enrique; López, J. Cristóbal; Gómez, Ana M.; Rio, Mayca del; Garcia, Inmaculada; Costela, Á.; Bañuelos, Jorge; Arbeloa, Teresa; Arbeloa, Í. López; Peña‐Cabrera, Eduardo

doi:10.1002/ejoc.201402767

Cited by 28 publications

(31 citation statements)

References 49 publications

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“…Carbohydrates have been labeled with BODIPY, leading to bright and photostable biological markers (Figure ) . In this regard, the linking unit (i.e., triazol or 8‐aryl sterically hindered) should be adequate to avoid intramolecular interactions or electronic couplings and retain the photophysical properties of the chromophore once the biomolecule is grafted.…”

Section: Discussionmentioning

confidence: 99%

BODIPY Dye, the Most Versatile Fluorophore Ever?

Bañuelos

2016

The Chemical Record

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257

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BODIPY laser dyes constitute a fascinating topic of research in modern photochemistry due to the large variety of options its chromophore offers, which is ready available for a multitude of synthetic routes. Indeed, in the literature one can find a huge battery of compounds based on the indacene core. The possibility of modulating the spectroscopic properties or inducing new photophysical processes by the substitution pattern of the BODIPY dyes has boosted the number of scientific and technological applications for these fluorophores. Along the following lines, I will overview the main results achieved in our laboratory with BODIPYs oriented to optoelectronic as well to biophotonic applications, stressing the more relevant photophysical issues to be considered in the design of a tailor-made BODIPY for a certain application and pointing out some of the remaining challenges.

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Section: Discussionmentioning

confidence: 99%

BODIPY Dye, the Most Versatile Fluorophore Ever?

Bañuelos

2016

The Chemical Record

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257

175

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“…Aside from boronic acids, arylstannanes were also good coupling partners in this procedure . With azido boronic acids, substrate 150 a could be converted into triazoles in one pot . In the presence of [Pd(PPh 3 ) 4 ] and CuDPP, the reactions could be completed within one hour in up to 90 % yield.…”

Section: Applicationsmentioning

confidence: 99%

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

et al. 2018

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The Pd-catalyzed, Cu I Àcarboxylate-mediated crosscoupling reactiono fo rganosulfur compounds with nucleophilic organometallic reagents is knowna st he Liebeskind-Srogl cross-coupling reaction. Owing to the readily available starting materials and neutral reactionc onditions, it has become an attractive procedure for the formation of carbonÀcarbon bonds, in particularf or cases in whicht radi-tional methods had failed. Since the seminal work of Liebeskind and Srogl in 2000, this reactionh as received intense attentionf rom the synthetic community.I nt his Focus Review,w eh ighlight recent advances in this intriguing cross-coupling reactiona nd its applications in organic synthesis.Scheme1.Liebeskind-Srogl cross-coupling reaction.Scheme2.The original Liebeskind-Sroglc ross-coupling reaction.d ba = dibenzylideneacetone, TFP = tri-2-furanylphosphine [a] Dr.Scheme4.Cross-coupling reaction between a-amino acid thiol esters and organostannanes. Cbz = benzyloxycarbonyl.Scheme5.Cross-coupling reaction between thiol esters and B-alkyl-9-BBN. 9-BBN = 9-borabicyclo[3.3.1]nonane.Scheme6.One-pothydroboration/intramolecular-cross-couplingr eaction between thiol esters and B-alkyl-9-BBN. DIPEA = N,N-diisopropylethylamine.Scheme7.Cross-coupling reaction between thiol esters andorganoindium reagents.Scheme8.Cross-coupling reaction between thiol esters andorganosilicon reagents. TBAF = tetra-n-butylammonium fluoride.Scheme9.Intramolecular cross-coupling reaction between thiol esters and olefins.Scheme38. Cross-coupling reaction between diaryld isulfides and boronicacids/terminal-alkynes.Scheme55. Synthesis of the C 15 ÀC 36 segment of goniodomin A. TBS = tert-butyldimethylsilyl, TBDPS = tert-butyldiphenylsilyl.Scheme56. To talsynthesis of verbenachalcone. MOM = methoxymethyl.Scheme57. Synthesis of enigmol and its stereoisomers. Boc = tert-butyloxycarbonyl.Scheme58. To talsynthesis of (À)-agelastatins A-F.Scheme59. Synthesis of quinone-containing salvinorin Aa nalogues.Scheme60. Synthesis of Soai-type aldehydes.

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“…[30] Access to BODIPYs 8b,w as initially carried out by an efficient Liebeskind-Srçgl cross-coupling reaction, [31] as described by PeÇa-Cabrera's group. [30] Access to BODIPYs 8b,w as initially carried out by an efficient Liebeskind-Srçgl cross-coupling reaction, [31] as described by PeÇa-Cabrera's group.…”

Section: Introductionmentioning

confidence: 99%

Solvent‐Sensitive Emitting Urea‐Bridged bis‐BODIPYs: Ready Access by a One‐Pot Tandem Staudinger/Aza‐Wittig Ureation

López

Rio

Oliden

et al. 2017

Chemistry A European J

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Herein we describe the synthesis, and computationally aided photophysical characterization of a new set of urea-bridged bis-BODIPY derivatives. These new dyads are efficiently obtained by a one-pot tandem Staudinger/aza-Wittig ureation protocol, from easily accessible meso-phenyl ortho-azidomethyl BODIPYs. These symmetric bis-BODIPYs outstand by a high absorption probability and excellent fluorescence and laser emission in less polar media. Nevertheless, this emission ability decreases in more polar media, which is ascribed to a light-induced charge-transfer from the urea spacer to the dipyrrin core, a process that can be modulated by appropriate changes in the substitution pattern of the BODIPY core. Furthermore, this ureation protocol can also be employed for the direct conjugation of our BODIPY-azides to amine-containing compounds, thus providing access to fluorescent non-symmetric ureas.

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Convenient Access to Carbohydrate–BODIPY Hybrids by Two Complementary Methods Involving One‐Pot Assembly of “Clickable” BODIPY Dyes

Cited by 28 publications

References 49 publications

BODIPY Dye, the Most Versatile Fluorophore Ever?

BODIPY Dye, the Most Versatile Fluorophore Ever?

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

Solvent‐Sensitive Emitting Urea‐Bridged bis‐BODIPYs: Ready Access by a One‐Pot Tandem Staudinger/Aza‐Wittig Ureation

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