Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of Aminoallenes via Selenium-π-Acid-Catalyzed Cross-Coupling of N-Fluorinated Sulfonimides with Simple Alkynes.

ABSTRACT: The facile synthesis of aminoallenes, accomplished by a selenium-π-acid-catalyzed cross-coupling of an N-fluorinated sulfonimide with simple, non-activated alkynes, is reported. Until now, aminoallenes were difficult to be accessed by customary means, inasmuch as pre-activated and, in part, intricate starting materials were necessary for their synthesis. In sharp contrast, the current study shows that ordinary internal alkynes can serve as simple and readily available precursors for the construction of the aminoallene motif. The operating reaction conditions tolerate numerous functional groups such as esters, nitriles, (silyl)ethers, acetals, and halogen substituents, furnishing the target compounds in up to 86 % yield.

SUBMITTER: Rode K

PROVIDER: S-EPMC7986078 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of Aminoallenes via Selenium-π-Acid-Catalyzed Cross-Coupling of <i>N</i>-Fluorinated Sulfonimides with Simple Alkynes.

Rode Katharina K Ramadas Narasimhamurthy Poorva P Rieger Rene R Krätzschmar Felix F Breder Alexander A

European journal of organic chemistry 20210308 11

The facile synthesis of aminoallenes, accomplished by a selenium-π-acid-catalyzed cross-coupling of an <i>N</i>-fluorinated sulfonimide with simple, non-activated alkynes, is reported. Until now, aminoallenes were difficult to be accessed by customary means, inasmuch as pre-activated and, in part, intricate starting materials were necessary for their synthesis. In sharp contrast, the current study shows that ordinary internal alkynes can serve as simple and readily available precursors for the c ...[more]

PMID: 33776555

Similar Datasets

Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling.

Project description:Herein, we report a highly effective protocol for the cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst tBuBrettPhos Pd G3 and Cs2CO3 in toluene. This Pd-catalyzed coupling features a short reaction time, excellent functional group tolerance, and compatibility with electron-rich and -poor (hetero)arenes. The method provides access to 18F-labeled trifluoroethyl ethers by cross-coupling with [18F]trifluoroethanol.

| S-EPMC7458480 | 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

Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis.

Project description:Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+2+1] pyrrole synthesis. Reactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido complexes yielded pentasubstituted 2-TMS-pyrroles with greater than 90 % selectivity over the other nine possible pyrrole products. The steric and electronic effects of the TMS group were both identified to play key roles in this highly selective pyrrole synthesis. This strategy provides a convenient method to synthesize multisubstituted pyrroles as well as an entry point for further pyrrole diversification through facile modification of the resulting 2-silyl pyrrole products, as demonstrated through a short formal synthesis of the marine natural product lamellarin R.

| S-EPMC5964026 | biostudies-literature

Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes.

Project description:An efficient copper-catalyzed cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes mediated by DDQ has been established. A protic additive, EtOH, proved to be crucial for harmonizing the oxidation with a subsequent alkynylation step by retaining the oxidation state of an oxocarbenium ion in the form of acetal. The CDC reaction exhibits a good substrate scope, with a range of terminal aryl- and alkyl alkynes being well tolerated. The copper-catalyzed alkynylation of 2H-chromene acetals with terminal alkynes was also explored.

| S-EPMC6051884 | biostudies-literature

Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling.

Project description:α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.

| S-EPMC6778098 | biostudies-literature

Copper-Catalyzed Oxidative Cross-Coupling of Electron-Deficient Polyfluorophenylboronate Esters with Terminal Alkynes.

Project description:We report herein a mild procedure for the copper-catalyzed oxidative cross-coupling of electron-deficient polyfluorophenylboronate esters with terminal alkynes. This method displays good functional group tolerance and broad substrate scope, generating cross-coupled alkynyl(fluoro)arene products in moderate to excellent yields. Thus, it represents a simple alternative to the conventional Sonogashira reaction.

| S-EPMC7821263 | biostudies-literature

Gold-Catalyzed Oxidative Coupling of Alkynes toward the Synthesis of Cyclic Conjugated Diynes.

Project description:A gold-catalyzed oxidative coupling of alkynes was developed as an efficient approach for the synthesis of challenging cyclic conjugated diynes (CCD). Compared to the classical copper-promoted oxidative coupling reaction of alkynes, this gold-catalyzed process exhibits a faster reaction rate due to the rapid reductive elimination from the Au(III) intermediate. This unique reactivity thus allowed a challenging diyne macrocyclization to take place in high efficiency. Condition screening revealed a [(n-Bu)4N]+[Cl-Au-Cl]- salt as the optimal pre-catalyst. Macrocycles with ring size between 13 to 28 atoms were prepared in moderate to good yields, which highlighted the broad substrate scope of this new strategy. Furthermore, the synthetic utilities of the cyclic conjugated diynes for copper-free click chemistry have been demonstrated, which showcased the potential application of this strategy in biological systems.

| S-EPMC6429935 | biostudies-literature

Aryl Radical Enabled, Copper-Catalyzed Sonogashira-Type Cross-Coupling of Alkynes with Alkyl Iodides

Project description: Not available

| S-EPMC10552849 | biostudies-literature

Allylic alcohol synthesis by Ni-catalyzed direct and selective coupling of alkynes and methanol.

Project description:Methanol is an abundant and renewable chemical raw material, but its use as a C1 source in C-C bond coupling reactions still constitutes a big challenge, and the known methods are limited to the use of expensive and noble metal catalysts such as Ru, Rh and Ir. We herein report nickel-catalyzed direct coupling of alkynes and methanol, providing direct access to valuable allylic alcohols in good yields and excellent chemo- and regioselectivity. The approach features a broad substrate scope and high atom-, step- and redox-economy. Moreover, this method was successfully extended to the synthesis of [5,6]-bicyclic hemiacetals through a cascade cyclization reaction of alkynones and methanol.

| S-EPMC8278963 | biostudies-literature

Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling.

Project description:A copper-catalyzed coupling of aryl, heteroaryl, and vinyl iodides with α-silyldifluoroamides is reported. The reaction forms α,α-difluoro-α-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