A copper-catalyzed cross-coupling of iodobenzoates with bromozinc-difluorophosphonate, generated from diethyl bromodifluoromethylphosphonate and zinc in dioxane, is reported. The notable features of this reaction are its high reaction efficiency, excellent functional group compatibility, and operational simplicity. This protocol provides a useful and facile access to aryldifluorophosphonates of interest in life science.
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http://dx.doi.org/10.1021/ol3006425 | DOI Listing |
Materials (Basel)
October 2020
Division of Materials Science, Graduate School of Environmental Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.
We have established a novel analytical method for solvent polarity on resin surface by combining the synthesis of fluorescent solvatochromic resin with optical waveguide spectrometry. The fluorescent solvatochromic resin was obtained via Suzuki-Miyaura cross-coupling between 4-iodobenzoic acid immobilized on Wang resin and 5-[4-(-dihexylamino)phenyl]-2-thienylboronic acid -methyl-iminodiacetic acid (MIDA) ester. The optical waveguide spectrometry studies on the resin showed a strong fluorescent solvatochromism in various organic solvents.
View Article and Find Full Text PDFMini Rev Med Chem
July 2018
Dr. Reddy's Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India.
Background: The 3,4-diyne substituted isocoumarins have been designed, synthesized and explored as potential anti-proliferative agents.
Method: Ultrasound assisted synthesis of these compounds was carried out by using a three-step method involving (i) Pd/C-Cu catalyzed cross-coupling between the methyl 2-iodobenzoate and buta- 1,3-diynylbenzene followed by (ii) I2-mediated electrophilic cyclization of the resultant 2-(alk-1- ynyl)benzoate ester and (iii) subsequent alkynylation of 4-iodo-3-(phenylethynyl)-isocoumarin under Pd/C-Cu catalysis.
Conclusion: The synthesized compounds showed promising growth inhibition when tested against MDA-MB 231 and K562 cancer cell lines.
ACS Comb Sci
October 2016
GlaxoSmithKline , Platform Technology & Science, ELT-Boston, 830 Winter Street, Waltham, Massachusetts 02451, United States.
DNA-encoded library technology (ELT) is a powerful tool for the discovery of new small-molecule ligands to various protein targets. Here we report the design and synthesis of biaryl DNA-encoded libraries based on the scaffold of 5-formyl 3-iodobenzoic acid. Three reactions on DNA template, acylation, Suzuki-Miyaura coupling and reductive amination, were applied in the library synthesis.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2015
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
Mild and regiocontrolled synthesis of a multisubstituted furan is achieved through Pd(OAc)2 -catalyzed room-temperature condensation of an alkynylbenziodoxole, a carboxylic acid, and an enolizable ketimine, which contribute to C1, CO, and C2 fragments, respectively, to the furan skeleton. The reaction tolerates a broad range of functional groups in each of the reaction components, and enables highly modular and flexible synthesis of variously substituted furans. The reaction is particularly effective for the rapid generation of tri- and tetraarylfurans and furan-containing oligoarylenes without relying on conventional cross-coupling chemistry.
View Article and Find Full Text PDFJ Am Chem Soc
September 2012
College of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230039, P.R. China.
C(sp(3))-C(sp) bond formations are of immense interest in chemistry and material sciences. We report herein a convenient, radical-mediated and catalytic method for C(sp(3))-C(sp) cross-coupling. Thus, with AgNO(3) as the catalyst and K(2)S(2)O(8) as the oxidant, various aliphatic carboxylic acids underwent decarboxylative alkynylation with commercially available ethynylbenziodoxolones in aqueous solution under mild conditions.
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