The donor–acceptor biphenyl platform: A versatile chromophore for the engineering of highly efficient two-photon sensitive photoremovable protecting groups

2012 ◽  
Vol 11 (3) ◽  
pp. 578 ◽  
Author(s):  
Alexandre Specht ◽  
Frédéric Bolze ◽  
Loïc Donato ◽  
Cyril Herbivo ◽  
Sébastien Charon ◽  
...  
Keyword(s):  
Protecting Groups ◽  
Two Photon ◽  
Highly Efficient ◽  
Photoremovable Protecting Groups ◽  
Donor Acceptor

Molecular Engineering of Photoremovable Protecting Groups for Two-Photon Uncaging

2008 ◽  
Vol 120 (49) ◽  
pp. 9667-9671 ◽  
Author(s):  
Sylvestre Gug ◽  
Frédéric Bolze ◽  
Alexandre Specht ◽  
Cyril Bourgogne ◽  
Maurice Goeldner ◽  
...  
Keyword(s):  
Molecular Engineering ◽  
Protecting Groups ◽  
Two Photon ◽  
Photoremovable Protecting Groups

Molecular Engineering of Photoremovable Protecting Groups for Two-Photon Uncaging

2008 ◽  
Vol 47 (49) ◽  
pp. 9525-9529 ◽  
Author(s):  
Sylvestre Gug ◽  
Frédéric Bolze ◽  
Alexandre Specht ◽  
Cyril Bourgogne ◽  
Maurice Goeldner ◽  
...  
Keyword(s):  
Molecular Engineering ◽  
Protecting Groups ◽  
Two Photon ◽  
Photoremovable Protecting Groups

scholarly journals Two-Photon Sensitive Coumarinyl Photoremovable Protecting Groups with Rigid Electron-Rich Cycles Obtained by Domino Reactions Initiated by a 5-exo-Dig Cyclocarbopalladation

2021 ◽  
Vol 23 (19) ◽  
pp. 7580-7585
Author(s):  
Juliane Chaud ◽  
Clément Morville ◽  
Frédéric Bolze ◽  
Delphine Garnier ◽  
Stefan Chassaing ◽  
...  
Keyword(s):  
Protecting Groups ◽  
Domino Reactions ◽  
Two Photon ◽  
Photoremovable Protecting Groups

scholarly journals Combinatorial discovery of two-photon photoremovable protecting groups

2003 ◽  
Vol 100 (22) ◽  
pp. 12548-12553 ◽  
Author(s):  
M. C. Pirrung ◽  
W. H. Pieper ◽  
K. P. Kaliappan ◽  
M. R. Dhananjeyan
Keyword(s):  
Protecting Groups ◽  
Two Photon ◽  
Photoremovable Protecting Groups

Water-Soluble, Donor-Acceptor Biphenyl Derivatives in the 2-(o-Nitrophenyl)propyl Series: Highly Efficient Two-Photon Uncaging of the Neurotransmitter γ-Aminobutyric Acid at λ=800 nm

2012 ◽  
Vol 124 (8) ◽  
pp. 1876-1879 ◽  
Author(s):  
Loïc Donato ◽  
Alexandre Mourot ◽  
Christopher M. Davenport ◽  
Cyril Herbivo ◽  
David Warther ◽  
...  
Keyword(s):  
Water Soluble ◽  
Aminobutyric Acid ◽  
Two Photon ◽  
Highly Efficient ◽  
Donor Acceptor

scholarly journals Two-Photon Excitable Photoremovable Protecting Groups Based on the Quinoline Scaffold for Use in Biology

2019 ◽  
Vol 85 (2) ◽  
pp. 726-744 ◽  
Author(s):  
Anna-Lisa K. Hennig ◽  
Davide Deodato ◽  
Naeem Asad ◽  
Cyril Herbivo ◽  
Timothy M. Dore
Keyword(s):  
Protecting Groups ◽  
Two Photon ◽  
Photoremovable Protecting Groups

Hafnium(IV) Chloride Catalyzes Highly Efficient Acetalization of Carbonyl Compounds

2019 ◽  
Vol 16 (6) ◽  
pp. 913-920 ◽  
Author(s):  
Israel Bonilla-Landa ◽  
Emizael López-Hernández ◽  
Felipe Barrera-Méndez ◽  
Nadia C. Salas ◽  
José L. Olivares-Romero
Keyword(s):  
Microwave Heating ◽  
Reaction Times ◽  
Protecting Groups ◽  
Catalyst Loading ◽  
Selective Protection ◽  
Highly Efficient ◽  
Aldehydes And Ketones ◽  
High Yields ◽  
Novel Catalyst ◽  
Acid Labile

Background: Hafnium(IV) tetrachloride efficiently catalyzes the protection of a variety of aldehydes and ketones, including benzophenone, acetophenone, and cyclohexanone, to the corresponding dimethyl acetals and 1,3-dioxolanes, under microwave heating. Substrates possessing acid-labile protecting groups (TBDPS and Boc) chemoselectively generated the corresponding acetal/ketal in excellent yields. Aim and Objective: In this study. the selective protection of aldehydes and ketones using a Hafnium(IV) chloride, which is a novel catalyst, under microwave heating was observed. Hence, it is imperative to find suitable conditions to promote the protection reaction in high yields and short reaction times. This study was undertaken not only to find a novel catalyst but also to perform the reaction with substrates bearing acid-labile protecting groups, and study the more challenging ketones as benzophenone. Materials and Methods: Using a microwave synthesis reactor Monowave 400 of Anton Paar, the protection reaction was performed on a raging temperature of 100°C ±1, a pressure of 2.9 bar, and an electric power of 50 W. More than 40 substrates have been screened and protected, not only the aldehydes were protected in high yields but also the more challenging ketones such as benzophenone were protected. All the products were purified by simple flash column chromatography, using silica gel and hexanes/ethyl acetate (90:10) as eluents. Finally, the protected substrates were characterized by NMR 1H, 13C and APCI-HRMS-QTOF. Results: Preliminary screening allowed us to find that 5 mol % of the catalyst is enough to furnish the protected aldehyde or ketone in up to 99% yield. Also it was found that substrates with a variety of substitutions on the aromatic ring (aldehyde or ketone), that include electron-withdrawing and electrondonating group, can be protected using this methodology in high yields. The more challenging cyclic ketones were also protected in up to 86% yield. It was found that trimethyl orthoformate is a very good additive to obtain the protected acetophenone. Finally, the protection of aldehydes with sensitive functional groups was performed. Indeed, it was found that substrates bearing acid labile groups such as Boc and TBDPS, chemoselectively generated the corresponding acetal/ketal compound while keeping the protective groups intact in up to 73% yield. Conclusion: Hafnium(IV) chloride as a catalyst provides a simple, highly efficient, and general chemoselective methodology for the protection of a variety of structurally diverse aldehydes and ketones. The major advantages offered by this method are: high yields, low catalyst loading, air-stability, and non-toxicity.

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