Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation.

ABSTRACT: A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product.

SUBMITTER: Huang C

PROVIDER: S-EPMC3250381 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation.

Huang Chunhui C Ghavtadze Nugzar N Chattopadhyay Buddhadeb B Gevorgyan Vladimir V

Journal of the American Chemical Society 20111018 44

A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product. ...[more]

PMID: 21999512

Similar Datasets

Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

Project description:A silanol-directed, Pd(II)-catalyzed C-H alkenylation of phenols is reported. This work features silanol, as a novel traceless directing group, and a directed o-C-H alkenylation of phenols. This new method allows for efficient synthesis of diverse alkenylated phenols, including an estrone derivative.

| S-EPMC3156791 | biostudies-literature

General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation.

Project description:A silanol-directed, palladium-catalyzed C-H carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional-group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o'-disubstituted phenolic compound through two sequential C-H functionalization processes.

| S-EPMC4565602 | biostudies-literature

Synthesis of cyclic guanidines via Pd-catalyzed alkene carboamination.

Project description:A new approach to the synthesis of substituted 5-membered cyclic guanidines is described. Palladium-catalyzed alkene carboamination reactions between acyclic N-allyl guanidines and aryl or alkenyl halides provide these products in good yield. This method allows access to a number of different cyclic guanidine derivatives in only two steps from readily available allylic amines.

| S-EPMC3857308 | biostudies-literature

Synthesis of polysubstituted tetrahydrofurans via Pd-catalyzed carboetherification reactions.

Project description:Pd-catalyzed carboetherifications of 1-, 2-, or 3-substituted γ-hydroxy internal alkenes afford tetrahydrofuran products bearing three stereocenters in good yield with moderate to good stereoselectivity.

| S-EPMC2752900 | biostudies-literature

Synthesis of chromans via Pd-catalyzed alkene carboetherification reactions.

Project description:A new method for the construction of 2-substituted and 2,2-disubstituted chromans via Pd-catalyzed carboetherification reactions between aryl/alkenyl halides and 2-(but-3-en-1-yl)phenols is described. These reactions effect formation of a C-O bond and a C-C bond to afford the chroman products in good yield, and also provide stereoselective access to tricyclic chroman derivatives.

| S-EPMC3319722 | biostudies-literature

Steric modulation of chiral biaryl diamines via Pd-catalyzed directed C-H arylation.

Project description:Palladium-catalyzed directed arylation of 2,2'-diacetamidobiaryls with aryl iodides provides efficient access to chiral ortho-substituted biaryl diamines. Aryl iodides with para- and meta-substituents are tolerated. Deprotection of the acetyl groups under basic conditions furnishes the free diamines, which should find broad utility in asymmetric catalysis.

| S-EPMC2726659 | biostudies-literature

Enantioconvergent synthesis of (+)-aphanorphine via asymmetric Pd-catalyzed alkene carboamination.

Project description:A concise asymmetric synthesis of (+)-aphanorphine has been achieved via a new enantioconvergent strategy. A racemic ?-aminoalkene derivative is transformed into a 1:1 mixture of enantiomerically enriched diastereomers using an asymmetric Pd-catalyzed carboamination. This mixture is then converted to an enantiomerically enriched protected aphanorphine derivative by a Friedel-Crafts reaction, which generates a quaternary all-carbon stereocenter. The natural product is obtained in three additional steps.

| S-EPMC3107030 | biostudies-literature

Synthesis of saturated 1,4-benzodiazepines via Pd-catalyzed carboamination reactions.

Project description:A new synthesis of 1,4-benzodiazepines and 1,4-benzodiazepin-5-ones is reported. The Pd-catalyzed coupling of N-allyl-2-aminobenzylamine derivatives with aryl bromides affords the heterocyclic products in good yield, and substrates bearing allylic methyl groups are transformed to cis-2,3-disubstituted products with >20:1 dr.

| S-EPMC3084890 | biostudies-literature

Unified synthesis of mono/bis-arylated phenols <i>via</i> Rh<sup>III</sup>-catalyzed dehydrogenative coupling.

Project description:2,6-Bis-arylated phenols are rarely reported and are synthetically challenging. Directed C-H functionalization reactions, using a directing group (DG), might provide a convenient solution to their synthesis. However, this strategy usually results in partial cleavage of the directing group, preventing further/second C-H activation cascades. Herein we report a general strategy that allows for the precise control of the oxidation pathways so that directing groups can be either preserved or cleaved. We found that N-phenoxyacetamides could undergo ortho-arylation reactions with or without an external oxidant, yielding products with different oxidation states, notably the rare bis-arylated phenols. Notably, a unique rhodacycle intermediate was isolated, characterized by X-ray crystallography, and confirmed to be an active catalyst. Switching between internal and external oxidation could be a general strategy in diverse directed C-H functionalization reactions to realize bis-functionalized products.

| S-EPMC5308286 | biostudies-literature

Synthesis of unsymmetrical diarylureas via Pd-catalyzed C-N cross-coupling reactions.

Project description:A facile synthesis of unsymmetrical N,N'-diarylureas is described. The utilization of the Pd-catalyzed arylation of ureas enables the synthesis of an array of diarylureas in good to excellent yields from benzylurea via a one-pot arylation-deprotection protocol, followed by a second arylation.

| S-EPMC3127456 | 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