Browse
Submit Data
Databases
API
Help

Dataset Information

13 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Aerobic Oxidative EDA Catalysis: Synthesis of Tetrahydroquinolines Using an Organocatalytic EDA Active Acceptor.

ABSTRACT: A catalytic electron donor-acceptor (EDA) complex for the visible-light-driven annulation reaction between activated alkenes and N,N-substituted dialkyl anilines is reported. The key photoactive complex is formed in situ between dialkylated anilines as donors and 1,2-dibenzoylethylene as a catalytic acceptor. The catalytic acceptor is regenerated by aerobic oxidation. Investigations into the mechanism are provided, revealing a rare example of a catalytic acceptor in photoactive EDA complexes that can give access to selective functionalization of aromatic amines under mild photochemical conditions.

SUBMITTER: Runemark A

PROVIDER: S-EPMC8790759 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Oxidative Amide Coupling from Functionally Diverse Alcohols and Amines Using Aerobic Copper/Nitroxyl Catalysis.

Project description:The aerobic Cu/ABNO catalyzed oxidative coupling of alcohols and amines is highlighted in the synthesis of amide bonds in diverse drug-like molecules (ABNO=9-azabicyclo[3.3.1]nonane N-oxyl). The robust method leverages the privileged reactivity of alcohols bearing electronegative hetero- atoms (O, F, N, Cl) in the ?-position. The reaction tolerates over 20 unique functional groups and is demonstrated on a 15?mmol scale under air. Steric constraints of the catalyst allow for chemoselective amidation of primary amines in the presence of secondary amines. All catalyst components are commercially available, and the reaction proceeds under mild conditions with retention of stereocenters in both reaction partners, while producing only water as a by-product.

| S-EPMC6707856 | biostudies-literature

?-Hydroxy-tetrahydroquinolines from Quinolines Using Chloroborane: Synthesis of the Peptidomimetic FISLE-412.

Project description:A new synthetic protocol provides a simple and direct method to generate functionalized ?-hydroxy-tetrahydroquinolines (THQs). Hydroboration of quinolines using chloroboranes followed by oxidation with NaBO3 ?H2 O led to the formation of functionalized ?-hydroxy THQs. High regio- and diastereoselectivities were observed in ? and ? substituted quinolines and the trans diastereomer of the ?-hydroxy-THQ was the major isostere. This new protocol was utilized to build the novel antibody-targeted lupus peptidomimetic, FISLE-412.

| S-EPMC6003427 | biostudies-literature

Synthesis of Formate Esters and Formamides Using an Au/TiO₂-Catalyzed Aerobic Oxidative Coupling of Paraformaldehyde.

Project description:A simple method for the synthesis of formate esters and formamides is presented based on the Au/TiO₂-catalyzed aerobic oxidative coupling between alcohols or amines and formaldehyde. The suitable form of formaldehyde is paraformaldehyde, as cyclic trimeric 1,3,5-trioxane is inactive. The reaction proceeds via the formation of an intermediate hemiacetal or hemiaminal, respectively, followed by the Au nanoparticle-catalyzed aerobic oxidation of the intermediate. Typically, the oxidative coupling between formaldehyde (2 equiv) and amines occurs quantitatively at room temperature within 4 h, and there is no need to add a base as in analogous coupling reactions. The oxidative coupling between formaldehyde (typically 3 equiv) and alcohols is unprecedented and occurs more slowly, yet in good to excellent yields and selectivity. Minor side-products (2-12%) from the acetalization of formaldehyde by the alcohol are also formed. The catalyst is recyclable and can be reused after a simple filtration in five consecutive runs with a small loss of activity.

| S-EPMC5746930 | biostudies-literature

Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.

Project description:Reported is the first enantioselective oxidative Pummerer-type transformation using phase-transfer catalysis to deliver enantioenriched sulfur-bearing heterocycles. This reaction includes the direct oxidation of sulfides to a thionium intermediate, followed by an asymmetric intramolecular nucleophilic addition to form chiral cyclic N,S-acetals with moderate to high enantioselectivites. Deuterium-labelling experiments were performed to identify the stereodiscrimination step of this process. Further analysis of the reaction transition states, by means of multidimensional correlations and DFT calculations, highlight the existence of a set of weak noncovalent interactions between the catalyst and substrate that govern the enantioselectivity of the reaction.

| S-EPMC5767526 | biostudies-literature

Site-Selective Aerobic C-H Monoacylation of Carbazoles Using Palladium Catalysis.

Project description:This manuscript describes the development of a remarkably general palladium-catalyzed monoacylation of carbazoles using toluene derivatives playing the dual role of acyl source and organic solvent. The method uses NHPI as the cocatalyst and oxygen as the sole oxidant. Interestingly, the acylation of monosubstituted N-pyridylcarbazoles takes place regioselectively at the C-8 position. The scope of the method is explored using aldehyde as the acyl source. This highly site-selective acylation proceeds through a radical process.

| S-EPMC7613175 | biostudies-literature

Organocatalytic Fluorogenic Synthesis of Chromenes.

Project description:Two fluorescent derivatives of 2-amino-3-carbonitrile-4H-chromene were synthesized by means of a fluorogenic Michael addition of dimedone to dicyano alkene labeled BODIPY derivatives. Different organocatalysts were used in different conditions to obtain compounds 3 and 4 in good yield (up to 65% and 85%) and moderate enantiomeric excess (51% and 41% ee, respectively). This work provides the first example of an enantioselective organocatalytic conversion combined with fluorogenesis.

| S-EPMC5393152 | biostudies-literature

Concerted Catalysis by Nanocellulose and Proline in Organocatalytic Michael Additions.

Project description:Cellulose nanofibers (CNFs) have recently attracted much attention as catalysts in various reactions. Organocatalysts have emerged as sustainable alternatives to metal-based catalysts in green organic synthesis, with concerted systems containing CNFs that are expected to provide next-generation catalysis. Herein, for the first time, we report that a representative organocatalyst comprising an unexpected combination of 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)-oxidized CNFs and proline shows significantly enhanced catalytic activity in an asymmetric Michael addition.

| S-EPMC6480416 | biostudies-literature

Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN<sup>3</sup> Pincer Catalyst.

Project description:A straightforward and selective synthesis of 1,2,3,4-tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy provides an atom-efficient pathway with water as the only byproduct. In addition, no further reducing agents are required.

| S-EPMC7587143 | biostudies-literature

Organocatalytic Enantiospecific Total Synthesis of Butenolides.

Project description:Biologically important, chiral natural products of butenolides, (-)-blastmycinolactol, (+)-blastmycinone, (-)-NFX-2, (+)-antimycinone, lipid metabolites, (+)-ancepsenolide, (+)-homoancepsenolide, mosquito larvicidal butenolide and their analogues were synthesized in very good yields in a sequential one-pot manner by using an organocatalytic reductive coupling and palladium-mediated reductive deoxygenation or organocatalytic reductive coupling and silica-mediated reductive deamination as the key steps.

| S-EPMC8306825 | biostudies-literature

Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines.

Project description:The four-component Hantzsch reaction provides access to pharmaceutically important dihydropyridines. To expand the utility of this method, we have developed a route under organocatalytic conditions with good yields and excellent ee's. Through catalyst screening, we found that a BINOL-phosphoric acid allowed enantioselective synthesis of six-membered heterocycles with a variety of substitution patterns.

| S-EPMC2727599 | 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