Browse
Submit Data
Databases
API
Help

Dataset Information

12 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Facile Synthesis of 3-Arylindenes by HMPA-Promoted Direct Arylation of Indenes with Aryl Fluorides.

ABSTRACT: A rapid and efficient approach to 3-arylated indenes by reactions of indenes with unactivated fluoroarenes with the assistance of lithium diisopropylamide and hexamethylphosphoramide at room temperature was developed.

SUBMITTER: Ji X

PROVIDER: S-EPMC6645374 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Facile Synthesis of 3-Arylindenes by HMPA-Promoted Direct Arylation of Indenes with Aryl Fluorides.

Ji Xinfei X Li Jialu J Wu Mingsheng M Cao Song S

ACS omega 20180829 8

A rapid and efficient approach to 3-arylated indenes by reactions of indenes with unactivated fluoroarenes with the assistance of lithium diisopropylamide and hexamethylphosphoramide at room temperature was developed. ...[more]

PMID: 31459139

Similar Datasets

A Copper-Catalyzed Arylation of Tryptamines for the Direct Synthesis of Aryl Pyrroloindolines.

Project description:An operationally simple, copper-catalyzed arylation of N-tosyltryptamines provides direct access to C3-aryl pyrroloindolines. A range of electron-donating and electron-withdrawing substituents is tolerated on both the indole backbone and the aryl electrophile. These reactions occur under ambient temperatures and with equimolar quantities of the coupling partners.

| S-EPMC3480223 | biostudies-literature

Application of Daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines.

Project description:A method for the direct arylation of benzotriazepines is reported, employing an aryl iodide as the coupling partner, copper iodide as the catalyst, and lithium tert-butoxide as the base. A variety of electron-rich, electron-poor, and sterically hindered aryl iodides are compatible with the reaction conditions. The arylation reaction can also be performed outside a glovebox in air without a significant decrease in yield. Furthermore, convenient microwave conditions for carrying out this transformation are reported.

| S-EPMC2674648 | biostudies-literature

Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.

Project description:An umpolung approach to the synthesis of diaryl ketones has been developed based on in situ generation of acyl anion equivalents and their catalytic arylation. This method entails the base promoted palladium catalyzed direct C-H arylation of 2 The resulting 2,2-diaryl-1,3-dithianes with aryl bromides. Use of MN(SiMe3)2 (M=Li, Na) base results in reversible deprotonation of the weakly acidic dithiane. In the presence of a Pd(NiXantphos)-based catalyst and aryl bromide, cross-coupling of the metallated 2-aryl-1,3-dithiane takes place under mild conditions (2 h at rt) with yields as high as 96%. The resulting 2,2-diaryl-1,3-dithianes were converted into diaryl ketones by either molecular iodine, N-bromo succinimide (NBS) or Selectfluor in the presence of water. The dithiane arylation/hydrolysis can be performed in a one-pot procedure to yield a good to excellent yields. This method is suitable for rapid and large-scale synthesis of diaryl ketones. A one-pot preparation of anti-cholesterol drug fenofibrate (TriCor®) has been achieved on 10.0 mmol scale in 86% yield.

| S-EPMC4500739 | biostudies-literature

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.

Project description:A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation successfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated.

| S-EPMC5369543 | biostudies-literature

Ag/Pd Cocatalyzed Direct Arylation of Fluoroarene Derivatives with Aryl Bromides.

Project description:Diverse C-H functionalizations catalyzed by Pd employ Ag(I) salts added as halide abstractors or oxidants. Recent reports have shown that Ag can also perform the crucial C-H activation step in several of these functionalizations. However, all of these processes are limited by the wasteful requirement for (super)stoichiometric Ag(I) salts. Herein, we report the development of a Ag/Pd cocatalyzed direct arylation of (fluoroarene) chromium tricarbonyl complexes with bromoarenes. The small organic salt, NMe4OC(CF3)3, added as a halide abstractor, enables the use of a catalytic amount of Ag, reversing the rapid precipitation of AgBr. We have shown through H/D scrambling and kinetic studies that a (PR3)Ag-alkoxide is responsible for C-H activation, a departure from previous studies with Ag carboxylates. Furthermore, the construction of biaryls directly from the simple arene is achieved via a one-pot chromium tricarbonyl complexation/C-H arylation/decomplexation sequence using (pyrene)Cr(CO)3 as a Cr(CO)3 donor.

| S-EPMC7079724 | biostudies-literature

A counteranion triggered arylation strategy using diaryliodonium fluorides.

Project description:A mild and transition metal-free counteranion triggered arylation strategy has been developed using diaryliodonium fluorides. The fluoride counteranion within the hypervalent iodonium species displays unusual reactivity that activates a phenolic O-H bond leading to electrophilic O-arylation. A wide range of phenols and diaryliodonium salts are compatible with this transformation under remarkably mild conditions. Furthermore, we pre-empt the wider implications of this strategy by demonstrating the compatibility of the arylation tactic with latent carbon nucleophiles.

| S-EPMC5811167 | biostudies-literature

Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides.

Project description:A Bi-catalyzed synthesis of sulfonyl fluorides from the corresponding (hetero)aryl boronic acids is presented. We demonstrate that the organobismuth(III) catalysts bearing a bis-aryl sulfone ligand backbone revolve through different canonical organometallic steps within the catalytic cycle without modifying the oxidation state. All steps have been validated, including the catalytic insertion of SO2 into Bi-C bonds, leading to a structurally unique O-bound bismuth sulfinate complex. The catalytic protocol affords excellent yields for a wide range of aryl and heteroaryl boronic acids, displaying a wide functional group tolerance.

| S-EPMC8719321 | biostudies-literature

Aryl Bromides and Aryl Chlorides for the Direct Arylation of Benzylic Amines Mediated by Ruthenium(II).

Project description:The ruthenium(II)-catalyzed sp3 C-H bond arylation of benzylic amines with aryl halides is reported. In the present method, aryl iodides and, more importantly, also the cheaper aryl bromides and aryl chlorides can be applied as aryl sources. Additionally, the method does not require elaborate manipulations in a glove box and can be carried out in simple screw cap vials. Potassium pivalate proved to be beneficial for the transformation with aryl bromides or iodides as aryl source, but was not required for aryl chlorides. In the latter case, the addition of PPh3 led to high conversion. 3-Methyl and 3-phenyl pyridine were established as directing groups, and the substituent in the 3-position represents a key structural feature for high conversion. The directing group can be cleaved after the transformation, which allows access to diarylmethylamines. Mechanistic studies were carried out and critically compared to mechanistic reports of related transformations.

| S-EPMC3698694 | biostudies-literature

Palladium-catalyzed direct C-H arylation of cyclic enaminones with aryl iodides.

Project description:A ligand-free method for the Pd-catalyzed direct arylation of cyclic enaminones using aryl iodides was developed. This method can be applied to a wide range of cyclic enaminones and aryl iodides with excellent C5-regioselectivity. Using widely available aryl iodides, the generality of this transformation provides easy access to a variety of 3-arylpiperidine structural motifs.

| S-EPMC3767375 | biostudies-literature

A General and Practical Palladium-Catalyzed Direct ?-Arylation of Amides with Aryl Halides.

Project description:An efficient system for the direct catalytic intermolecular ?-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indole-based phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic ?-protons of amides (pKa up to 35) were reversibly depotonated by LiO t Bu, NaO t Bu, or NaN(SiMe3)2.

| S-EPMC3994175 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data