Browse
Submit Data
Databases
API
Help

Dataset Information

13 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.

ABSTRACT: An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl triflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.

SUBMITTER: Liu Z

PROVIDER: S-EPMC2627407 | biostudies-other | 2006 Apr

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.

Liu Zhijian Z Larock Richard C RC

The Journal of organic chemistry 20060401 8

An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl triflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups. ...[more]

PMID: 16599619

Similar Datasets

N-Arylation of amines, amides, imides and sulfonamides with arylboroxines catalyzed by simple copper salt/EtOH system.

Project description:The coupling of arylboroxines with a variety of amines, amides, imides and sulfonamides catalyzed by a copper salt/EtOH system has been developed. In the absence of a base or additive the corresponding N-arylation products were obtained in moderate to excellent yields.

| S-EPMC2587945 | biostudies-literature

Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes.

Project description:A facile and modular synthesis of triarylmethanes was achieved in good yield via a two-step sequence in which the final step is the copper(II)-catalyzed arylation of diarylmethanols with arylboronic acids. By using this protocol a variety of symmetrical and unsymmetrical triarylmethanes were synthesized. As an application of the newly developed methodology, we demonstrate a high-yielding synthesis of the triarylmethane intermediate towards an anti-breast-cancer drug candidate.

| S-EPMC4902010 | biostudies-literature

Redox-neutral α-arylation of amines.

Project description:The direct α-arylation/N-alkylation of cyclic amines was achieved in a redox-neutral fashion under mild conditions. Transformations occur in the absence of any additives or are promoted by simple carboxylic acids.

| S-EPMC3946350 | biostudies-literature

Palladium-Catalyzed ?-Arylation of Methyl Sulfonamides with Aryl Chlorides.

Project description:A Palladium-catalyzed ?-arylation of sulfonamides with aryl chlorides is presented. A Buchwald type precatalyst formed with Kwong's indole-based ligand enabled this transformation to be compatible with a large variety of methyl sulfonamides and aryl chlorides in good to excellent yields. Importantly, under the optimized reaction conditions, only mono-arylated products were observed. This method has been applied to the efficient synthesis of sumatriptan, which is used to treat migraines.

| S-EPMC5218594 | biostudies-literature

Direct transition-metal-free intramolecular arylation of phenols.

Project description:Direct transition-metal-free, base-mediated intramolecular arylation of phenols with aryl halides has been developed. In the presence of 2.5 equiv of t-BuOK in dioxane at 140 degrees C, the intramolecular cyclization of 3-(2-halobenzyloxy)phenols affords 6H-benzo[c]chromenes in high yields. This reaction proceeds by an initial formation of a benzyne intermediate followed by an aromatic sp(2) C-H functionalization (a formal C-H activation) to form the carbon-carbon bond.

| S-EPMC2627406 | biostudies-literature

Synthesis of benzannelated sultams by intramolecular Pd-catalyzed arylation of tertiary sulfonamides.

Project description:A new and efficient approach to five- and six-membered benzannelated sultams by intramolecular C-arylation of tertiary 1-(methoxycarbonyl)methanesulfonamides under palladium catalysis is described. In case of the ?-toluenesulfonamide derivative, an unexpected formation of a 2,3-diarylindole was observed under the same conditions.

| S-EPMC5629375 | biostudies-literature

Catalyst-free arylation of sulfonamides <i>via</i> visible light-mediated deamination.

Project description:A novel arylation of sulfonamides with boronic acids to afford numerous diaryl sulfones via a visible light-mediated N-S bond cleavage other than the typical transition-metal-catalyzed C(O)-N bond activation is described. This methodology, which represents the first catalyst-free protocol for the sulfonylation of boronic acids, is characterized by its simple reaction conditions, good functional group tolerance and high efficiency. Several successful examples for the late-stage functionalization of diverse sulfonamides indicate the high potential utility of this method in pharmaceutical science and organic synthesis.

| S-EPMC8279011 | biostudies-literature

Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) <i>via</i> trifluoroborate-iminiums (TIMs).

Project description:We report the facile formation of trifluoroborate-iminiums (TIMs) from potassium acyltrifluoroborates (KATs) and the transformation of TIMs to α-aminotrifluoroborates by reduction or Grignard additions. Conditions for the hydrolysis of α-aminotrifluoroborates to α-aminoboronic acids, which are important biologically active compounds, were established. This new methodology allows access to sterically demanding α-aminoboronic acids that are not easily prepared with currently available methods. This work also introduces TIMs, that can be easily prepared and handled, as a new category of functional groups that serve as precursors to valuable organic compounds.

| S-EPMC6000978 | biostudies-literature

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles.

Project description:Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.

| S-EPMC5512281 | biostudies-literature

Copper-Catalyzed, Ceric Ammonium Nitrate Mediated N-Arylation of Amines.

Project description:Cu-Catalyzed, ligand and base free cross-coupling of aryl boronic acids with primary and secondary amines has been reported. This 'Chan-Evans-Lam' reaction has revealed that at room temperature, catalytic copper(II) acetate and ceric ammonium nitrate (CAN) as an oxidant, N-arylation can result in an effective C-N bond formation. This air stable, practical, robust protocol enables a variety of functional group tolerance on both boronic acid and amine partners.

| S-EPMC6419960 | 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