Browse
Submit Data
Databases
API
Help

Dataset Information

15 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Decarboxylative Polyfluoroarylation of Alkylcarboxylic Acids.

ABSTRACT: Polyfluoroarenes are useful building blocks in several areas such as drug discovery, materials, and crop protection. Herein, we report the first polyfluoroarylation of aliphatic carboxylic acids via photoredox decarboxylation. The method proceeds with broad substrate scope and high functional group tolerance. Moreover, small complex molecules such as natural products and drugs can be modified by late-stage modification.

SUBMITTER: Sun X

PROVIDER: S-EPMC8252513 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Decarboxylative Hydroxylation of Benzoic Acids.

Project description:Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

| S-EPMC8596882 | biostudies-literature

Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids.

Project description:Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, alcohols, and strained ring systems. To demonstrate the broad potential of this new methodology for late-stage functionalization, we successfully converted a diverse array of carboxylic acid-bearing natural products and medicinal agents to the corresponding trifluoromethyl analogues.

| S-EPMC6538506 | biostudies-literature

Enantioselective decarboxylative chlorination of ?-ketocarboxylic acids.

Project description:Stereoselective halogenation is a highly useful organic transformation for multistep syntheses because the resulting chiral organohalides can serve as precursors for various medicinally relevant derivatives. Even though decarboxylative halogenation of aliphatic carboxylic acids is a useful and fundamental synthetic method for the preparation of a variety of organohalides, an enantioselective version of this reaction has not been reported. Here we report a highly enantioselective decarboxylative chlorination of ?-ketocarboxylic acids to obtain ?-chloroketones under mild organocatalytic conditions. The present method is also applicable for the enantioselective synthesis of tertiary ?-chloroketones. The conversions of the resulting ?-chloroketones into ?-aminoketones and ?-thio-substituted ketones via SN2 reactions at the tertiary carbon centres are also demonstrated. These results constitute an efficient approach for the synthesis of chiral organohalides and are expected to enhance the availability of enantiomerically enriched chiral compounds with heteroatom-substituted chiral stereogenic centres.

| S-EPMC5465354 | biostudies-literature

Decarboxylative Annulation of ?-Amino Acids with ?-Ketoaldehydes.

Project description:Indolizidine and quinolizidine derivatives are readily assembled from l-proline or (±)-pipecolic acid and ?-ketoaldehydes via a decarboxylative annulation process. These reactions are promoted by acetic acid and involve azomethine ylides as reactive intermediates.

| S-EPMC5937137 | biostudies-literature

Decarboxylative Annulation of ?-Amino Acids with ?-Nitroaldehydes.

Project description:Indolizidine and quinolizidine derivatives are readily assembled from proline or pipecolic acid and ?-nitroaldehydes by means of a decarboxylative annulation process. These reactions are promoted by simple acetic acid and involve azomethine ylides as reactive intermediates. The method was applied to the synthesis of an epiquinamide analog.

| S-EPMC5013532 | biostudies-literature

A highly selective decarboxylative deuteration of carboxylic acids.

Project description:In this paper, we report a mild and practical method for precise deuteration of aliphatic carboxylic acids by synergistic photoredox and HAT catalysis. The reaction delivers excellent D-incorporation (up to 99%) at predicted sites even in substrates bearing reactive C-H bonds or versatile functional groups. The use of a recirculation reactor with a peristaltic pump supports a scalable preparative ability (up to 50 mmol) under very mild reaction conditions. The practical and precise deuteration of readily available complex carboxylic acids makes this protocol promising for the preparation of deuterium-labelled compounds.

| S-EPMC8179560 | biostudies-literature

Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

Project description:The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F(•) transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

| S-EPMC4862610 | biostudies-literature

Decarboxylative hydrazination of unactivated carboxylic acids by cerium photocatalysis.

Project description:We report the cerium photocatalyzed radical decarboxylative hydrazination of carboxylic acids with di-tert-butylazodicarboxylate (DBAD). The operationally simple protocol provides rapid access to synthetically useful hydrazine derivatives and overcomes current scope limitations in the photoredox-catalyzed decarboxylation of carboxylic acids.

| S-EPMC6498423 | biostudies-literature

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids.

Project description:Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

| S-EPMC5935059 | biostudies-literature

Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.

Project description:A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant ?-amino and phenylacetic allyl esters. This operationally simple process produces CO2 as the only byproduct and provides direct access to allylated alkanes. After photochemical oxidation, the carboxylate undergoes radical decarboxylation to site-specifically generate radical intermediates which undergo allylation. A radical dual catalysis mechanism is proposed. Free phenylacetic acids were also allylated utilizing similar reactions conditions.

| S-EPMC4183636 | 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