Browse
Submit Data
Databases
API
Help

Dataset Information

19 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Rh(iii)-catalyzed C-H olefination of N-pentafluoroaryl benzamides using air as the sole oxidant.

ABSTRACT: The oxidative olefination of a broad array of arenes and heteroarenes with a variety of activated and unactivated olefins has be achieved via a rhodium(iii)-catalyzed C-H activation reaction. The use of an N-pentafluorophenyl benzamide directing group is crucial for achieving catalytic turnovers in the presence of air as the sole oxidant without using a co-oxidant.

SUBMITTER: Lu Y

PROVIDER: S-EPMC5810239 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Rh(iii)-catalyzed C-H olefination of N-pentafluoroaryl benzamides using air as the sole oxidant.

Lu Yi Y Wang Huai-Wei HW Spangler Jillian E JE Chen Kai K Cui Pei-Pei PP Zhao Yue Y Sun Wei-Yin WY Yu Jin-Quan JQ

Chemical science 20150108 3

The oxidative olefination of a broad array of arenes and heteroarenes with a variety of activated and unactivated olefins has be achieved via a rhodium(iii)-catalyzed C-H activation reaction. The use of an N-pentafluorophenyl benzamide directing group is crucial for achieving catalytic turnovers in the presence of air as the sole oxidant without using a co-oxidant. ...[more]

PMID: 29449919

Similar Datasets

Iron-Catalyzed Oxidative C-O and C-N Coupling Reactions Using Air as Sole Oxidant.

Project description:We describe the oxygenation of tertiary arylamines, and the amination of tertiary arylamines and phenols. The key step of these coupling reactions is an iron-catalyzed oxidative C-O or C-N bond formation which generally provides the corresponding products in high yields and with excellent regioselectivity. The transformations are accomplished using hexadecafluorophthalocyanine-iron(II) (FePcF16 ) as catalyst in the presence of an acid or a base additive and require only ambient air as sole oxidant.

| S-EPMC9314016 | biostudies-literature

Rhodium-Catalyzed Electrooxidative C-H Olefination of Benzamides.

Project description:Metal-catalyzed chelation-assisted C-H olefinations have emerged as powerful tools for the construction of functionalized alkenes. Herein, we describe the rhoda-electrocatalyzed C-H activation/alkenylation of arenes. The olefinations of challenging electron-poor benzamides were thus accomplished in a fully dehydrogenative fashion under electrochemical conditions, avoiding stoichiometric chemical oxidants, and with H2 as the only byproduct. This versatile alkenylation reaction also features broad substrate scope and used electricity as a green oxidant.

| S-EPMC7496262 | biostudies-literature

Rh(III)-Catalyzed Annulation of Boc-Protected Benzamides with Diazo Compounds: Approach to Isocoumarins.

Project description:A mild rhodium-catalyzed annulation of Boc-protected benzamides with diazo compounds via C-C/C-O bond formation has been explored. In the presence of [Cp*RhCl₂]₂, AgSbF₆ and Cs₂CO₃, Boc-protected benzamides can be effectively annulated to yield isocoumarins in 0.5⁻2 h.

| S-EPMC6429621 | biostudies-literature

Iron-Catalyzed Oxidative C-C Cross-Coupling Reaction of Tertiary Anilines with Hydroxyarenes by Using Air as Sole Oxidant.

Project description:A mild procedure for the oxidative C-C cross-coupling of tertiary anilines with phenols is described which provides the products generally in high yields and with excellent selectivity. The reaction is catalyzed by the hexadecafluorinated iron-phthalocyanine complex FePcF16 in the presence of substoichiometric amounts of methanesulfonic acid and ambient air as sole oxidant.

| S-EPMC7064917 | biostudies-literature

Pd(II)-catalyzed C-H iodination using molecular I2 as the sole oxidant.

Project description:Pd-catalyzed ortho-C-H iodination directed by a weakly coordinating amide auxiliary using I2 as the sole oxidant was developed. This reaction is compatible with a wide range of heterocycles including pyridines, imidazoles, oxazoles, thiazoles, isoxazoles, and pyrazoles.

| S-EPMC3762701 | biostudies-literature

A coupling of benzamides and donor/acceptor diazo compounds to form ?-lactams via Rh(III)-catalyzed C-H activation.

Project description:The coupling of O-pivaloyl benzhydroxamic acids with donor/acceptor diazo compounds provides isoindolones in high yield. The reaction tolerates a broad range of benzhydroxamic acids and diazo compounds, including substituted 2,2,2-trifluorodiazoethanes. Mechanistic experiments suggested that C-H activation is turnover-limiting and irreversible and that insertion of the diazo compound favors electron-deficient substrates.

| S-EPMC3658175 | biostudies-literature

Urea-Substituted Tetramethylcyclopentadienyl Ligands for Supramolecularly Accelerated RhIII -Catalyzed ortho-C-H Olefination of Benzoic Acid Derivatives.

Project description:The design and synthesis of air-stable and conveniently crystallizable RhIII -cyclopentadienyl catalysts substituted with a urea moiety, which are able to accelerate the C-H olefination of benzoic acid derivatives, is reported. Through kinetic studies and NMR titration experiments, the catalysts' substrate recognition ability mediated by hydrogen bonding was identified to be the reason for this effect. Introduction of pyridone-phosphine ligands capable of forming additional H-bond interactions increased the catalytic performance even further. By unveiling a proportionality between reaction rate and relative complex formation enthalpy the hypothesis of a supramolecular catalyst preformation was supported. Its application to a variety of substrates proved the catalyst system's advantages, generally increasing the yields when compared to the results obtained with widely used [RhCp*Cl2 ]2 .

| S-EPMC7898290 | biostudies-literature

Rhodium(III)-catalyzed oxidative carbonylation of benzamides with carbon monoxide.

Project description:An efficient strategy for the oxidative carbonylation of aromatic amides via C-H/N-H activation to form phthalimides using an Rh(III) catalyst has been developed. The reaction shows a preference for C-H bonds of electron-rich aromatic amides and tolerates a variety of functional groups.

| S-EPMC3423973 | biostudies-literature

An unusual endo-selective C-H hydroarylationof norbornene by the Rh(I)-catalyzed reactionof benzamides.

Project description:Hydroarylation is an environmentally attractive strategy which incorporates all of the atoms contained in the substrates into the desired products. Almost all the hydroarylations of norbornene reported to date involve an exo-selective reaction. Here we show the endo-selective hydroarylation of norbornene in the Rh(I)-catalyzed reaction of aromatic amides. The addition of sterically bulky carboxylic acids enhances the endo-selectivity of the reaction. The results of deuterium-labeling experiments show that both the ortho-carbon and the ortho-hydrogen atoms of aromatic amides were attached to the same carbon atom of the norbornane skeleton in the hydroarylation product. These results clearly suggest that hydrometalation or carbometalation, which are commonly accepted mechanisms for the catalytic hydroarylation of C-H bonds, are not involved as the key step in the present reaction, and suggest that the reaction involves a rhodium carbene complex generated from norbornene as the key intermediate.

| S-EPMC5682280 | biostudies-literature

Silver-Catalyzed Aldehyde Olefination Using Siloxy Alkynes.

Project description:We describe the development of a silver-catalyzed carbonyl olefination employing electron rich siloxy alkynes. This process constitutes an efficient synthesis of trisubstituted unsaturated esters, and represents an alternative to the widely utilized Horner-Wadsworth-Emmons reaction. Excellent diastereoselectivities are observed for a range of aldehydes using either 1-siloxy-1-propyne or 1-siloxy-1-hexyne. This mild catalytic process also enables chemoselective olefination of aldehydes in the presence of either ester or ketone functionality. Furthermore, since no by-products are generated, this catalytic process is perfectly suited for development of sequential reactions that can be carried out in a single flask.

| S-EPMC3837490 | biostudies-literature