Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: 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.

SUBMITTER: Rao HS

PROVIDER: S-EPMC4902010 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

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

Rao H Surya Prakash HS Rao A Veera Bhadra AV

Beilstein journal of organic chemistry 20160311

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. ...[more]

PMID: 27340442

Similar Datasets

Copper-assisted palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids.

Project description:Described herein is a palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids. The versatility of this method is that both electron-rich and electron-poor boronic acids can be coupled in high yields. A mixture of two Cu(II) additives was crucial for efficient cross-coupling. The role of each Cu(II) reagent appears to be distinct and complementary serving to assist catalyst reoxidation and transmetalation through a putative arylcopper intermediate.

| S-EPMC3490213 | biostudies-literature

Copper(II)-Mediated [<sup>11</sup>C]Cyanation of Arylboronic Acids and Arylstannanes.

Project description:A copper-mediated method for the transformation of diverse arylboron compounds and arylstannanes to aryl-[11C]-nitriles is reported. This method is operationally simple, uses commercially available reagents, and is compatible with a wide variety of substituted aryl- and heteroaryl substrates. This method is applied to the automated synthesis of high specific activity [11C]perampanel in 10% nondecay-corrected radiochemical yield (RCY).

| S-EPMC5892454 | biostudies-literature

Direct C-H arylation of electron-deficient heterocycles with arylboronic acids.

Project description:A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate co-oxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method allows for rapid access to a variety of arylated heterocycles that would be more difficult to access with traditional methods.

| S-EPMC2946225 | biostudies-literature

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

Project description: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.

| S-EPMC2627407 | biostudies-literature

Silver-mediated trifluoromethoxylation of aryl stannanes and arylboronic acids.

Project description:A silver-mediated cross-coupling of trifluoromethoxide with aryl stannanes and arylboronic acids to give aryl trifluoromethyl ethers is reported. This is the first report of a transition-metal-mediated C(aryl)-OCF(3) bond formation.

| S-EPMC3218431 | biostudies-literature

Regioselective Arylation of Quinoline N-Oxides (C8), Indolines (C7) and N-tert-Butylbenzamide with Arylboronic Acids.

Project description:Herein, we disclose Ru(II)-catalyzed regioselective distal C(sp2)-H arylation of quinoline N-oxide with arylboronic acids to 8-arylquinolines. In the developed method, the Ru(II)-catalyst shows dual activity, that is, distal C-H activation of quinoline N-oxides followed by in situ deoxygenation of arylated quinoline N-oxide in the same pot. The current catalytic method features use of Ru metal as the catalyst and arylboronic acids as the arylating source under mild reaction conditions. Use of the Rh(III)-catalyst in place of Ru(II) under the same conditions afforded 8-arylquinoline N-oxides with excellent regioselectivity. Furthermore, the developed Ru(II) catalytic system is also extended for the C(sp2)-H arylation of indolines, N-tert-butylbenzamide, and 6-(5H)-phenanthridinone. Formation of the quinoline N-oxide coordinated ruthenium adduct is found to be the key reaction intermediate, which has been characterized by single crystal X-ray diffraction and NMR spectroscopy.

| S-EPMC6964538 | biostudies-literature

Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst.

Project description:N-aryl imidazoles play an important role as structural and functional units in many natural products and biologically active compounds. Herein, we report a photocatalytic route for the C-N cross-coupling reactions over a Cu/graphene catalyst, which can effectively catalyze N-arylation of imidazole and phenylboronic acid, and achieve a turnover frequency of 25.4 h(-1) at 25°C and the irradiation of visible light. The enhanced catalytic activity of the Cu/graphene under the light irradiation results from the localized surface plasmon resonance of copper nanoparticles. The Cu/graphene photocatalyst has a general applicability for photocatalytic C-N, C-O and C-S cross-coupling of arylboronic acids with imidazoles, phenols and thiophenols. This study provides a green photocatalytic route for the production of N-aryl imidazoles.

| S-EPMC4648406 | biostudies-other

Palladium-Catalyzed C2-Selective Direct Arylation of Benzo[<i>b</i>]thiophene 1,1-Dioxides with Arylboronic Acids.

Project description:A novel oxidative cross-coupling of benzo[b]thiophene 1,1-dioxides with arylboronic acids was reported. The efficient reaction occurred at the C2-position via C-H activation, followed by Pd(II)-catalyzed arylation. Furthermore, a series of C2-arylated products with significant photoluminescence properties have been synthesized and characterized, which illustrates the potential applications of our method in the aggregation-induced emission field.

| S-EPMC10785645 | biostudies-literature

Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids.

Project description:A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.

| S-EPMC3766840 | biostudies-literature

Catalytic Enantioselective Synthesis of 3-Piperidines from Arylboronic Acids and Pyridine.

Project description:Piperidines are frequently found in natural products and are of importance to the pharmaceutical industry. A generally useful asymmetric route to enantiomerically enriched 3-substituted piperidines remains elusive. Here we report a cross-coupling approach to enantioenriched 3-piperidines from pyridine- and sp2-hybridized boronic acids. The key step involves a Rh-catalyzed asymmetric reductive Heck reaction of aryl, heteroaryl, or vinyl boronic acids and phenyl pyridine-1(2H)-carboxylate to provide 3-substituted tetrahydropyridines in high yield and excellent enantioselectivity with a wide functional group tolerance. A three-step process involving i) partial reduction of pyridine, ii) Rh-catalyzed asymmetric carbometalation, and then iii) another reduction provides access to a wide variety of enantioenriched 3-piperidines, including clinically used materials such as Preclamol and Niraparib.

| S-EPMC10326878 | 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