Browse
Submit Data
Databases
API
Help

Dataset Information

27 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.

ABSTRACT: The synthesis of 3,3-difluoro-2-oxindoles through a robust and efficient palladium-catalyzed C?H difluoroalkylation is described. This process generates a broad range of difluorooxindoles from readily prepared starting materials. The use of BrettPhos as the ligand was crucial for high efficiency. Preliminary mechanistic studies suggest that oxidative addition is the rate-determining step for this process.

SUBMITTER: Shi SL

PROVIDER: S-EPMC4384468 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.

Shi Shi-Liang SL Buchwald Stephen L SL

Angewandte Chemie (International ed. in English) 20141204 5

The synthesis of 3,3-difluoro-2-oxindoles through a robust and efficient palladium-catalyzed CH difluoroalkylation is described. This process generates a broad range of difluorooxindoles from readily prepared starting materials. The use of BrettPhos as the ligand was crucial for high efficiency. Preliminary mechanistic studies suggest that oxidative addition is the rate-determining step for this process. ...[more]

PMID: 25476241

Similar Datasets

Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation.

Project description:Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical arsenal, including bimolecular alkene hydroarylation reactions. We report here a broad-scope, palladium-catalyzed pyrroline hydroarylation process that gives 3-aryl pyrrolidines, a class of small molecules with potency in a diverse range of biological scenarios. Thus, whereas N-acyl pyrrolines usually undergo palladium-catalyzed arylation to give alkene products, the corresponding reactions of N-alkyl pyrrolines deliver products of hydroarylation, pyrrolidines. The process has broad substrate scope and can be used to directly deliver drug-like molecules in a single step from readily available precursors.

| S-EPMC6240703 | biostudies-literature

Synthesis of substituted isoquinolines utilizing palladium-catalyzed ?-arylation of ketones.

Project description:The utilization of sequential palladium-catalyzed ?-arylation and cyclization reactions provides a general approach to an array of isoquinolines and their corresponding N-oxides. This methodology allows the convergent combination of readily available precursors in a regioselective manner and in excellent overall yields. This powerful route to polysubstituted isoquinolines, which is not limited to electron rich moieties, also allows rapid access to analogues of biologically active compounds.

| S-EPMC3406859 | biostudies-other

Synthesis of Pyridine-Fused Siloles by Palladium-Catalyzed Intramolecular Bis-Silylation.

Project description:Silole derivatives are attracting significant attention as new functional materials with excellent electronic and photophysical properties. Thus, the development of synthesis methods to afford such derivatives is highly desirable. Herein, the synthesis of pyridine-fused siloles under the conditions of the Sonogashira coupling reaction is described. The reactions of 2-bromo-3-(pentamethyldisilanyl)pyridine (1) with ethynylbenzene derivatives in the presence of PdCl2(PPh3)2-CuI as a catalyst afforded the corresponding pyridine-fused siloles (2a-2c) through intramolecular trans-bis-silylation. DFT calculations were also performed to understand the reaction mechanism. This paper is the first to report on the successful use of palladium catalysts in the trans-bis-silylation of alkynes with disilanes.

| S-EPMC9435037 | biostudies-literature

Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides.

Project description:An expeditious approach to the construction of spiroindenyl-2-oxindoles was developed via a palladium-catalyzed spirocyclization reaction of 2-bromoarylamides with vinyl bromides. The reaction formed spiropalladacycles as the intermediates via carbopalladation and the C-H functionalization of 2-bromoarylamides. The spiropalladacycles reacted with vinyl bromides to form spiroindenyl-2-oxindoles. A Heck process rather than vinylic C-H functionalization was involved in the reaction.

| S-EPMC8704520 | biostudies-literature

Non-Palladium-Catalyzed Approach to the Synthesis of (<i>E</i>)-3-(1,3-Diarylallylidene)Oxindoles.

Project description:Two novel synthetic approaches for synthesizing (E)-3-(1,3-diarylallylidene)oxindoles from oxindole were developed. All previously reported methods for synthesizing 3-(1,3-diarylallylidene)oxindoles utilized palladium-catalyzed reactions as a key step to form this unique skeleton. Despite high efficiency, palladium-catalyzed reactions have limitations in terms of substrate scope. Especially, an iodoaryl moiety cannot be introduced by the previous methods due to its high reactivity toward the palladium catalyst. Our Knoevenagel/allylic oxidation/Wittig and Knoevenagel/aldol/dehydration strategies complement each other and show broad substrate scope, including substrates with iodoaryl groups. The current methods utilized acetophenones, benzylidene phosphonium ylides, and benzaldehydes that are commercially available or easily accessible. Thus, the current synthetic approaches to (E)-3-(1,3-diarylallyldiene)oxindoles are readily amendable for variety of oxindole derivatives.

| S-EPMC9415770 | biostudies-literature

Palladium-Catalyzed Intramolecular Oxidative Arylations for the Synthesis of Fused Biaryl Sulfones.

Project description:This study unveils palladium-catalyzed intramolecular oxidative cyclizations in biaryl and heterobiaryl sulfones providing direct access to fused biaryl sulfones (dibenzothiophene-5,5-dioxides). Variously substituted dibenzothiophene-5,5-dioxides could be readily prepared in good to excellent yields under optimized conditions. In addition, bromination afforded dibromo derivative of dibenzothiophene-5,5-dioxides, providing platform for late-stage diversification. The translational applications of this current protocol have successfully been demonstrated in the synthesis of 2,8-diamino derivative of dibenzothiophene-5,5-dioxides, a α7-nicotinic acetylcholine receptor agonist analogue, and novel single fluorene-tethered dibenzothiophene-5,5-dioxide, an organic emitter.

| S-EPMC6641745 | biostudies-literature

Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles.

Project description:We report here a novel method for the modular synthesis of highly substituted piperazines and related bis-nitrogen heterocycles via a palladium-catalyzed cyclization reaction. The process couples two of the carbons of a propargyl unit with various diamine components to provide nitrogen heterocycles in generally good to excellent yields and high regio- and stereochemical control.

| S-EPMC4991562 | biostudies-literature

Synthesis of substituted tetrahydroindoloisoquinoline derivatives via intramolecular Pd-catalyzed alkene carboamination reactions.

Project description:Intramolecular Pd-catalyzed alkene carboamination reactions of substituted 2-allyl-N-(2-bromobenzyl)anilines are described. The substrates for these reactions are generated in two steps from readily available 2-allylanilines and 2-bromobenzaldehyde derivatives. The transformations afford substituted tetrahydroindoloisoquinolines, an uncommon class of fused bicyclic heterocycles, in good yield. The mechanism of these transformations is described, and a model that accounts for the observed product stereochemistry is proposed.

| S-EPMC4011572 | biostudies-literature

Palladium-Catalyzed One-Pot Approach to 3-(Diarylmethylene)oxindoles from Propiolamidoaryl Triflate.

Project description:3-(Diarylmethylene)oxindoles have been synthesized from propiolamidoaryl triflate utilizing a palladium-catalyzed one-pot reaction consisting of three successive reactions: Sonogashira, Heck, and Suzuki-Miyaura. This method allows for the production of a complex skeleton of 3-(diarylmethylene)oxindole from propiolamidoaryl triflate using a commercially available aryl iodide and arylboronic acid in a simple and efficient way with moderate yield and stereoselectivity.

| S-EPMC6331821 | biostudies-other

Advanced palladium free approach to the synthesis of substituted alkene oxindoles <i>via</i> aluminum-promoted Knoevenagel reaction.

Project description:A synthetic route for the synthesis of C24, as well as for the design of focused libraries of direct AMPK activators was developed based on a convergent strategy. The proposed scheme corresponds to the current trends in C-H bond functionalization. The use of aluminum isopropoxide for the Knoevenagel condensation of oxindole with benzophenones is a noticeable point of this work.

| S-EPMC9086994 | 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