Browse
Submit Data
Databases
API
Help

Dataset Information

31 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Copper-catalysed regioselective sulfenylation of indoles with sodium sulfinates.

ABSTRACT: A copper-catalysed sulfenylation of indoles with sodium sulfinates that affords 3-sulfenylindoles in good-to-excellent yields in N,N-dimethyl formamide (DMF) is described. In the process, DMF serves not only as a solvent but also as a reductant. This transformation is easy to carry out and has mild reaction conditions and good functional group tolerance.

SUBMITTER: Luo X

PROVIDER: S-EPMC5990840 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Copper-catalysed regioselective sulfenylation of indoles with sodium sulfinates.

Luo Xiaojun X Liu Qiang Q Zhu Hongxia H Chen Huoji H

Royal Society open science 20180530 5

A copper-catalysed sulfenylation of indoles with sodium sulfinates that affords 3-sulfenylindoles in good-to-excellent yields in N,N-dimethyl formamide (DMF) is described. In the process, DMF serves not only as a solvent but also as a reductant. This transformation is easy to carry out and has mild reaction conditions and good functional group tolerance. ...[more]

PMID: 29892452

Similar Datasets

Copper-Catalyzed Redox Coupling of Nitroarenes with Sodium Sulfinates.

Project description:A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.

| S-EPMC6479299 | biostudies-literature

An umpolung-enabled copper-catalysed regioselective hydroamination approach to α-amino acids.

Project description:A copper-catalysed regio- and stereoselective hydroamination of acrylates with hydrosilanes and hydroxylamines has been developed to afford the corresponding α-amino acids in good yields. The key to regioselectivity control is the use of hydroxylamine as an umpolung, electrophilic amination reagent. Additionally, a judicious choice of conditions involving the CsOPiv base and DTBM-dppbz ligand of remote steric hindrance enables the otherwise challenging C-N bond formation at the α position to the carbonyl. The point chirality at the β-position is successfully controlled by the Xyl-BINAP or DTBM-SEGPHOS chiral ligand with similarly remote steric bulkiness. The combination with the chiral auxiliary, (-)-8-phenylmenthol, also induces stereoselectivity at the α-position to form the optically active unnatural α-amino acids with two adjacent stereocentres.

| S-EPMC8409476 | biostudies-literature

Copper-Catalyzed Synthesis of Masked (Hetero)Aryl Sulfinates.

Project description:Catalysis using substoichiometric copper facilitates the synthesis of masked (hetero)aryl sulfinates under mild, base-free conditions from aryl iodides and the commercial sulfonylation reagent sodium 1-methyl 3-sulfinopropanoate (SMOPS). The development of a tert-butyl ester variant of the SMOPS reagent allowed the use of aryl bromide substrates. The sulfones thus generated can be unmasked and functionalized in situ to form a variety of sulfonyl-containing functional groups.

| S-EPMC11020165 | biostudies-literature

Unbiased C3-Electrophilic Indoles: Triflic Acid Mediated C3-Regioselective Hydroarylation of N-H Indoles.

Project description:The direct dearomative addition of arenes to the C3 position of unprotected indoles is reported under operationally simple conditions, using triflic acid at room temperature. The present regioselective hydroarylation is a straightforward manner to generate an electrophilic indole at the C3 position from unbiased indoles in sharp contrast to previous strategies. This atom-economical method delivers biologically relevant 3-arylindolines and 3,3-spiroindolines in high yields and regioselectivities from both intra- and intermolecular processes. DFT computations suggest the stabilization of cationic or dicationic intermediates with H-bonded (TfOH)n clusters.

| S-EPMC9401073 | biostudies-literature

Ligand-Mediated and Copper-Catalyzed C(sp(3))-H Bond Functionalization of Aryl Ketones with Sodium Sulfinates under Mild Conditions.

Project description:A novel and convenient copper (II) bromide and 1,8-diazabicyclo[5.4.1]undec-7-ene (DBU) or 1,10-phenanthroline catalysis protocol for the construction of α-alkyl-β-keto sulfones via C(sp(3))-H bond functionalization followed by C(sp(3))-S bond formation between aryl ketones and sodium sulfinates at room temperature has been developed. This method is applicable to a wide range of aryl ketones and sodium sulfinates. The electronic effects of aryl ketones and ligands effects of the copper salts are crucial for this transformation. Typically, substituted aryl ketones with electron-withdrawing group do not need any ligand to give a good to excellent yield, while substituted aryl ketones with electron-donating group and electron-rich heteroaromatic ketones offer a good to excellent yield only under the nitrogen-based ligands. The practical value of this transformation highlights the efficient and robust one-pot synthesis of α-alkyl-β-keto sulfones.

| S-EPMC4683520 | biostudies-literature

Copper-promoted sulfenylation of sp2 C-H bonds.

Project description:An auxiliary-assisted, copper catalyzed or promoted sulfenylation of benzoic acid derivative ?-C-H bonds and benzylamine derivative ?-C-H bonds has been developed. The method employs disulfide reagents, copper(II) acetate, and DMSO solvent at 90-130 °C. Application of this methodology to the direct trifluoromethylsulfenylation of C-H bonds was demonstrated.

| S-EPMC3498454 | biostudies-literature

Boron Trifluoride Etherate Promoted Regioselective 3-Acylation of Indoles with Anhydrides.

Project description:An efficient, high-yielding and scalable procedure for the regioselective 3-acylation of indoles with anhydrides promoted by boron trifluoride etherate under mild conditions was reported. This novel protocol provided a simple way to prepare 3-(benzofuran-2-yl) indole in three steps.

| S-EPMC9741063 | biostudies-literature

I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.

Project description:Readily available triethylammonium thiolates were proven to be new and eco-friendly sulfenylating agents for the efficient and practical construction of sulfenylated indoles and pyrroles (48 examples) with good to excellent yields under metal-free and microwave irradiation conditions. The combination of I2 and DMSO enabled direct C-S bond formation, allowing easy and low-cost access to new functionalized C,S-tethered bisindoles and pyrrole-indole pairs with a wide diversity of substituents. The mechanism involving S-S and S-I bond-forming/breaking events was proposed.

| S-EPMC5624724 | biostudies-literature

Electrochemical Alkoxysulfonylation Difunctionalization of Styrene Derivatives Using Sodium Sulfinates as Sulfonyl Sources.

Project description:An eco-friendly method for the synthesis of β-alkoxy sulfones via electrochemical alkoxysulfonylation reaction of styrenes with sodium sulfinates as sulfonyl sources has been established. The reaction is conducted in an undivided cell at room temperature and tolerates a wide scope of styrenes, sodium sulfinates, and alcohols. The reaction does not need any chemical oxidants and transition-metal catalysts, which provides a new and green access to β-alkoxy sulfones.

| S-EPMC6733175 | biostudies-literature

Iridium-catalysed regioselective borylation of carboranes via direct B-H activation.

Project description:Carboranes are carbon-boron molecular clusters, which can be viewed as three-dimensional analogues to benzene. They are finding many applications in medicine, materials and organometallic chemistry. On the other hand, their exceptional thermal and chemical stabilities, as well as 3D structures, make them very difficult to be functionalized, in particular the regioselective functionalization of BH vertex among ten similar B-H bonds. Here we report a very efficient iridium-catalysed borylation of cage B(3,6)-H bonds of o-carboranes with excellent yields and regioselectivity using bis(pinacolato)diboron (B2pin2) as a reagent. Selective cage B(4)-H borylation has also been achieved by introducing a bulky TBDMS (tert-butyldimethylsilyl) group to one cage carbon vertex. The resultant 3,6-(Bpin)2-o-carboranes are useful synthons for the synthesis of a wide variety of B(3,6)-difunctionalized o-carboranes bearing cage B-X (X=O, N, C, I and Br) bonds.

| S-EPMC5357313 | 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