The synthesis of arylCF2CF2SiMe3 and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-arylethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 °C or room temperature are the key features of this Cu-Ag mediated cross-coupling methodology. The chemistry is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chemistry.
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http://dx.doi.org/10.1021/acs.orglett.5b01510 | DOI Listing |
ACS Appl Mater Interfaces
December 2024
College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China.
Programming and synthesizing bifunctional materials for regulating the output of triboelectric nanogenerators (TENGs) and their photocatalytic efficiency is a promising strategy for energy harvesting to build self-powered systems. Herein, we tackle this challenge by introducing metal-organic frameworks (MOFs) as molecular catalysts and triboelectric layers for self-powered photocatalytic systems. A zeolite-like mixed-valence MOF () and a ladder-structured MOF () were obtained through structural transformation.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2022
Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Diaryl difluoromethanes are valuable targets for medicinal chemistry because they are bioisosteres of diaryl ethers and can function as replacements for diaryl methane, ketone, and sulfone groups. However, methods to prepare diaryl difluoromethanes are scarce, especially methods starting from abundant aryl halides. We report the Pd-catalyzed aryldifluoromethylation of aryl halides with aryldifluoromethyl trimethylsilanes (TMSCF Ar).
View Article and Find Full Text PDFJ Org Chem
March 2022
Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.
To synthesize -ethynylene-conjugated porphyrin arrays, the Sonogashira cross-coupling reaction is straightforward to construct the C(sp)-C(sp) bonds, but the reaction is often accompanied by side reactions such as the Glaser homocoupling. The rate-determining oxidative addition step results in the unexpected kinetic competition with the Glaser homocoupling, which is desired to be circumvented. We here propose two sets of improved strategies for the synthesis of arylene-ethynylene-linked porphyrin arrays from the -brominated porphyrin and alkynes.
View Article and Find Full Text PDFOrg Lett
July 2015
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, OX1 3TA Oxford, U.K.
The synthesis of arylCF2CF2SiMe3 and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-arylethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 °C or room temperature are the key features of this Cu-Ag mediated cross-coupling methodology. The chemistry is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chemistry.
View Article and Find Full Text PDFAcc Chem Res
May 2014
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science , 345 Lingling Lu, Shanghai 200032, China.
The trifluoromethyl group is widely prevalent in many pharmaceuticals and agrochemicals because its incorporation into drug candidates could enhance chemical and metabolic stability, improve lipophilicity and bioavailability, and increase the protein bind affinity. Consequently, extensive attention has been devoted toward the development of efficient and versatile methods for introducing the CF3 group into various organic molecules. Direct trifluoromethylation reaction has become one of the most efficient and important approaches for constructing carbon-CF3 bonds.
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