Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes.

ABSTRACT: A direct assembly of secondary benzylureas and related amine derivatives via copper-catalyzed carboamination of styrenes with potassium alkyltrifluoroborates and ureas, anilines, or an amide is reported. Terminal and 1,2-disubstituted alkenes, as well as dienes, participate in this three-component coupling reaction. The reaction mechanism likely involves the addition of an alkyl radical to the styrene, followed by metal-mediated oxidative coupling of the resulting benzylic radical with the amine derivative. Factors that impact substrate reactivity and regioselectivity are discussed.

SUBMITTER: Kennedy-Ellis JJ

PROVIDER: S-EPMC8170827 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes.

Kennedy-Ellis Jonathan J JJ Boldt Erik D ED Chemler Sherry R SR

Organic letters 20201019 21

A direct assembly of secondary benzylureas and related amine derivatives via copper-catalyzed carboamination of styrenes with potassium alkyltrifluoroborates and ureas, anilines, or an amide is reported. Terminal and 1,2-disubstituted alkenes, as well as dienes, participate in this three-component coupling reaction. The reaction mechanism likely involves the addition of an alkyl radical to the styrene, followed by metal-mediated oxidative coupling of the resulting benzylic radical with the amine ...[more]

PMID: 33074005

Similar Datasets

Cu-Catalyzed Three-Component Carboamination of Alkenes.

Project description:Copper-catalyzed intermolecular carboamination of alkenes with α-halocarbonyls and amines is presented with 42 examples. Electron rich, electron poor, and internal styrenes, as well as α-olefins, are functionalized with α-halocarbonyls and aryl or aliphatic amines. Mechanistic investigations suggest the reaction is proceeding through addition of a carbon-centered radical across an olefin followed by oxidation to form a 5-membered oxocarbenium intermediate and subsequent nucleophilic ring opening to forge the C-N bond.

| S-EPMC6092015 | 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

Cu-Catalyzed Three-Component Carboamination of Electron Deficient Olefins.

Project description:The copper-catalyzed three-component carboamination of atropates for the synthesis of α-aryl amino acid derivatives is presented. The scope of the reaction is explored with respect to all three coupling partners: the alkyl halide, the atropate, and the aryl amine. A total of 41 examples are included, with yields of ≤92%. Both primary and secondary aryl amines participate in the carboamination along with α-haloesters, nitriles, and perfluoroiodoalkanes. Mechanistic investigations support a radical mechanism involving Cu-mediated C-N bond formation with the radical adduct.

| S-EPMC10771120 | biostudies-literature

Organic-photoredox-catalyzed three-component sulfonylative pyridylation of styrenes.

Project description:An efficient, metal-free protocol for the three-component sulfonylative pyridylation of styrenes via organic-photoredox catalysis is described. This metal-free process enables the direct and selective installation of sulfonyl and heteroaryl motifs and tolerates a wide array of functional groups as well as complex molecular scaffolds, that could complement previous methods and would be of interest in pharmaceutical research.

| S-EPMC8691066 | biostudies-literature

6-Azabicyclo[3.2.1]octanes Via Copper-Catalyzed Enantioselective Alkene Carboamination.

Project description:Bridged bicyclic rings containing nitrogen heterocycles are important motifs in bioactive small organic molecules. An enantioselective copper-catalyzed alkene carboamination reaction that creates bridged heterocycles is reported herein. Two new rings are formed in this alkene carboamination reaction where N-sulfonyl-2-aryl-4-pentenamines are converted to 6-azabicyclo[3.2.1]octanes using [Ph-Box-Cu](OTf)2 or related catalysts in the presence of MnO2 as stoichiometric oxidant in moderate to good yields and generally excellent enantioselectivities. Two new stereocenters are formed in the reaction, and the C-C bond-forming arene addition is a net C-H functionalization.

| S-EPMC4254729 | biostudies-literature

Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives.

Project description:A copper-catalyzed aminooxygenation reaction of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives has been developed. The aminooxygenation product could be converted into the corresponding alcohol or free amine through the cleavage of the N-O or C-N bond of the N-hydroxyphthalimide moiety.

| S-EPMC4734344 | biostudies-literature

Efficient and General Synthesis of 3-Aminoindolines and 3-Aminoindoles via Copper-Catalyzed Three Component Coupling Reaction.

Project description:An efficient three component coupling (TCC) reaction toward a variety of 3-aminoindoline and 3-aminoindole derivatives has been developed. This cascade transformation proceeds via the copper-catalyzed coupling reaction between 2-aminobenzaldehyde, secondary amine, and alkyne leading to propargylamine intermediate, which, under the reaction conditions, undergoes cyclization into the indoline core. The latter, upon treatment with a base, smoothly isomerizes into indole. Alternatively, indole can directly be synthesized in a one-pot sequential reaction.

| S-EPMC3633492 | 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 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

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 γ-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

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