Browse
Submit Data
Databases
API
Help

Dataset Information

31 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts.

ABSTRACT: Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable, synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents.

SUBMITTER: Qin L

PROVIDER: S-EPMC4824678 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts.

Qin Linlin L Hu Bao B Neumann Kiel D KD Linstad Ethan J EJ McCauley Katelyenn K Veness Jordan J Kempinger Jayson J JJ DiMagno Stephen G SG

European journal of organic chemistry 20150814 27

Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable, synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents. ...[more]

PMID: 27065751

Similar Datasets

Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone.

Project description:A straightforward synthesis of diaryliodonium salts is achieved by using Oxone as the stoichiometric oxidant. Slow addition is the key to obtaining good yields and purities of the reaction products, which are highly useful reagents in many different areas of organic synthesis.

| S-EPMC5288754 | biostudies-literature

One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts.

Project description:A transition-metal-free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one-pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryliodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2]?ligand coupling pathway.

| S-EPMC5089574 | biostudies-literature

One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone-sulfuric acid.

Project description:A facile synthesis of diaryliodonium salts utilizing Oxone as versatile and cheap oxidant has been developed. This method shows wide applicability and can be used for the preparation of iodonium salts containing electron-donating or electron-withdrawing groups in good yields. In addition, this procedure can be applied to the preparation of symmetric iodonium salts directly from arenes via a one-pot iodination-oxidation sequence.

| S-EPMC5905280 | biostudies-literature

The Diaryliodonium(III) Salts Reaction With Free-Radicals Enables One-Pot Double Arylation of Naphthols.

Project description:The chemoselective reaction of the C- followed by the O-centered naphthyl radicals with the more electron-deficient hypervalent bond of the diaryliodonium(III) salts is described. This discovered reactivity constitutes a new activation mode of the diaryliodonium(III) salts which enabled a one-pot doubly arylation of naphthols through the sequential C s p 2 - C s p 2 /O- C s p 2 bond formation. The naphthyl radicals were generated in the reaction by the tetramethylpiperidinyl radical (TMP·) which resulted from the homolytic fragmentation of the precursor TMP2O. Experimental and DFT calculations provided a complete panorama of the reaction mechanism.

| S-EPMC7593783 | biostudies-literature

Isothiourea-mediated one-pot synthesis of functionalized pyridines.

Project description:Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/lactamization, thiophenol elimination, and N- to O-sulfonyl migration, giving 2-sulfonate-substituted pyridines which are readily derivatized to generate structural diversity.

| S-EPMC4065352 | biostudies-literature

One-pot facile and mild construction of densely functionalized pyrimidines in water <i>via</i> consecutive C-C and C-S bonds formation.

Project description:Fused pyrimidines composed of alternating heteroatoms and a pyrimidine moiety were synthesized efficiently using readily available starting material 4-hydroxycoumarin, aromatic aldehydes, and urea/thiourea at room temperature. Acid, metal salts, and surfactants were screened for their influence on catalytic activity in three-component reactions and sodium lauryl sulphate (SLS) was used as the best catalyst with different concentrations. Screening results of catalyst loading from our investigation showed that good to excellent yields were obtained with 10 mol%. Our method efficiently synthesized heterocycles and avoided the use of hazardous solvents and conventional organic solvents. Our procedure which involves a surfactant is operationally simple, environmentally benign, has excellent yields, short reaction times, and synthetically is as efficient as conventional procedures using organic solvents.

| S-EPMC9086688 | biostudies-literature

One-pot synthesis and applications of N-heteroaryl iodonium salts.

Project description:An efficient one-pot synthesis of N-heteroaryl iodonium triflates from the corresponding N-heteroaryl iodide and arene has been developed. The reaction conditions resemble our previous one-pot syntheses, with suitable modifications to allow N-heteroaryl groups. The reaction time is only 30?min, and no anion exchange is required. The obtained iodonium salts were isolated in a protonated form, these salts can either be employed directly in applications or be deprotonated prior to use. The aryl groups were chosen to induce chemoselective transfer of the heteroaryl moiety to various nucleophiles. The reactivity and chemoselectivity of these iodonium salts were demonstrated by selectively introducing a pyridyl moiety onto both oxygen and carbon nucleophiles in good yields.

| S-EPMC3943608 | biostudies-literature

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8.

Project description:Various 4-aryl-3-bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3-aryl-2-propynoic acids with diaryliodonium triflates and K2CO3 in the presence of CuCl, followed by the reaction with tetrabutylammonium bromide (TBAB) and Na2S2O8. The obtained 3-bromo-4-phenylcoumarin was transformed into 4-phenylcoumarin derivatives bearing C-H, C-S, C-N, and C-C bonds at 3-position.

| S-EPMC5815302 | biostudies-literature

Catalyst-Free One-Pot Synthesis of Densely Substituted Pyrazole-Pyrazines as Anti-Colorectal Cancer Agents.

Project description:The first catalyst-free post-Ugi cascade methodology was developed for expeditious access to structurally diverse and complex pyrazole-pyrazines in one-pot. This novel cascade reaction features an intramolecular N2-arylation of pyrazoles with allenes at the C-β position of triple bond. Screening in the colorectal cancer cell lines HCT116 and SW620 validated the feasibility of the methodology for generating bioactive compounds. The lead compound 7h which is active against HCT116 and SW620 with IC50 of 1.3 and 1.8 µM, respectively, can be synthesized and purified in a gram process synthetic scale in 7 hours. The mechanical studies indicated that compound 7h can induce cell cycle arrest in the G2/M phase and inhibit proliferation and viability in human colon cancer cells. Overall, compound 7h is represented as a promising starting point for the development of new anti-colorectal cancer drugs.

| S-EPMC7283261 | biostudies-literature

Three-Component One-Pot Synthesis of Highly Functionalized Bis-Indole Derivatives.

Project description:In this study, we detail the development of a concise and efficient three-component protocol for the regioselective synthesis of highly functionalized bis-indoles through a one-pot, two-step sequential process starting from enaminones 1, indoles 2, and acenaphthylene-1,2-dione 3 that is catalyzed by piperidine and p-methyl benzenesulfonic acid. This protocol has several advantages including simplicity of experimental operation, high efficiency of bond formation, ready availability and low cost of starting materials, environmentally benign conditions, and target molecular diversity.

| S-EPMC6682060 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

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