Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A general method for copper-catalyzed arene cross-dimerization.

ABSTRACT: A general method for a highly regioselective copper-catalyzed cross-coupling of two aromatic compounds using iodine as an oxidant has been developed. The reactions involve an initial iodination of one arene followed by arylation of the most acidic C-H bond of the other coupling component. Cross-coupling of electron-rich arenes, electron-poor arenes, and five- and six-membered heterocycles is possible in many combinations. Typically, a 1/1.5 to 1/3 ratio of coupling components is used, in contrast to existing methodology that often employs a large excess of one of the arenes. Common functionalities such as ester, ketone, aldehyde, ether, nitrile, nitro, and amine are well-tolerated.

SUBMITTER: Do HQ

PROVIDER: S-EPMC3168561 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A general method for copper-catalyzed arene cross-dimerization.

Do Hien-Quang HQ Daugulis Olafs O

Journal of the American Chemical Society 20110808 34

A general method for a highly regioselective copper-catalyzed cross-coupling of two aromatic compounds using iodine as an oxidant has been developed. The reactions involve an initial iodination of one arene followed by arylation of the most acidic C-H bond of the other coupling component. Cross-coupling of electron-rich arenes, electron-poor arenes, and five- and six-membered heterocycles is possible in many combinations. Typically, a 1/1.5 to 1/3 ratio of coupling components is used, in contras ...[more]

PMID: 21823581

Similar Datasets

A general method for copper-catalyzed arylation of arene C-H bonds.

Project description:A general method for copper-catalyzed arylation of sp (2) C-H bonds with p K a's below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K 3PO 4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can be arylated. Furthermore, electron-poor arenes possessing at least two electron-withdrawing groups on a benzene ring can also be arylated. Two arylcopper-phenanthroline complex intermediates were independently synthesized.

| S-EPMC2740489 | biostudies-other

Copper-catalyzed arene C-H bond cross-coupling.

Project description:A highly regioselective, one-pot sequential iodination-copper-catalyzed cross-coupling of arene C-H bonds has been developed affording an efficient method for biaryl synthesis.

| S-EPMC2828042 | biostudies-literature

Nickel, manganese, cobalt, and iron-catalyzed deprotonative arene dimerization.

Project description:A number of first-row transition metal salts catalyze deprotonative dimerization of acidic arenes. Under the atmosphere of oxygen, nickel, manganese, cobalt, and iron chlorides have been shown to dimerize five- and six-membered ring heterocycles as well as electron-poor arenes. Both tetramethylpiperidide and dicyclohexylamide bases can be employed; however, the former afford slightly higher yields.

| S-EPMC2840611 | biostudies-literature

Copper-Catalyzed Dimerization/Cyclization of Itaconates.

Project description:A copper-catalyzed domino reaction between itaconate esters and diethyl zinc (or silane) is developed, affording itaconate dimerization products, multi-ester-substituted cyclopentanones, in moderate to high yields.

| S-EPMC6332366 | biostudies-literature

Copper-catalyzed etherification of arene C-H bonds.

Project description:A method for direct, auxiliary-assisted alkoxylation and phenoxylation of ?-sp(2) C-H bonds of benzoic acid derivatives and ?-sp(2) C-H bonds of amine derivatives is reported. The reaction employs (CuOH)2CO3 catalyst, air as an oxidant, phenol or alcohol coupling partner, DMF, pyridine, or DMPU solvent, and K2CO3, tetramethylguanidine, or K3PO4 base at 70-130 °C.

| S-EPMC3880618 | biostudies-literature

A General Method for Aminoquinoline-Directed, Copper-Catalyzed sp(2) C-H Bond Amination.

Project description:An operationally simple and general method for copper-catalyzed, aminoquinoline-assisted amination of ?-C(sp(2))-H bonds of benzoic acid derivatives is reported. The reaction employs Cu(OAc)2 or (CuOH)2CO3 catalysts, an amine coupling partner, and oxygen from air as a terminal oxidant. Exceptionally high generality with respect to amine coupling partners is observed. Specifically, primary and secondary aliphatic and aromatic amines, heterocycles, such as indoles, pyrazole, and carbazole, sulfonamides, as well as electron-deficient aromatic and heteroaromatic amines are competent coupling components.

| S-EPMC4829344 | biostudies-literature

Copper-Catalyzed Homo-Dimerization of Nitronates and Enolates under Oxygen Atmosphere.

Project description:A method for copper-catalyzed oxidative dimerization of nitronates and enolates using oxygen as terminal oxidant has been developed. Cyclization through oxidative intramolecular coupling is also feasible for both nitronates and enolates. The mild reaction conditions lead to good functional group tolerance.

| S-EPMC3568985 | biostudies-literature

Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

Project description:We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of ?-sp(2) C-H bonds of benzoic acid derivatives and ?-sp(2) C-H bonds of ?,?-disubstituted benzylamine derivatives. The reaction employs a CuI catalyst, a AgF fluoride source, and DMF, pyridine, or DMPU solvent at moderately elevated temperatures. Selective mono- or difluorination can be achieved by simply changing reaction conditions. The method shows excellent functional group tolerance and provides a straightforward way for the preparation of ortho-fluorinated benzoic acids.

| S-EPMC3733384 | biostudies-literature

Selective Manganese-Catalyzed Dimerization and Cross-Coupling of Terminal Alkynes.

Project description:Herein, efficient manganese-catalyzed dimerization of terminal alkynes to afford 1,3-enynes is described. This reaction is atom economic, implementing an inexpensive, earth-abundant nonprecious metal catalyst. The precatalyst is the bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dippe)(CO)3(CH2CH2CH3)]. The catalytic process is initiated by migratory insertion of a CO ligand into the Mn-alkyl bond to yield an acyl intermediate that undergoes rapid C-H bond cleavage of alkyne, forming an active Mn(I) acetylide catalyst [Mn(dippe)(CO)2(C≡CPh)(η2-HC≡CPh)] together with liberated butanal. A range of aromatic and aliphatic terminal alkynes were efficiently and selectively converted into head-to-head Z-1,3-enynes and head-to-tail gem-1,3-enynes, respectively, in good to excellent yields. Moreover, cross-coupling of aromatic and aliphatic alkynes selectively yields head-to-tail gem-1,3-enynes. In all cases, the reactions were performed at 70 °C with a catalyst loading of 1-2 mol %. A mechanism based on density functional theory (DFT) calculations is presented.

| S-EPMC8185884 | biostudies-literature

Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling.

Project description:A copper-catalyzed coupling of aryl, heteroaryl, and vinyl iodides with ?-silyldifluoroamides is reported. The reaction forms ?,?-difluoro-?-aryl amides from electron-rich, electron-poor, and sterically hindered aryl iodides in high yield and tolerates a variety of functional groups. The aryldifluoroamide products can be transformed further to provide access to a diverse array of difluoroalkylarenes, including compounds of potential biological interest.

| S-EPMC4956475 | 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