An efficient palladium-catalyzed route for tandem synthesis of imidazole-fused polyheterocycles from 2-vinyl imidazoles and aryl halides is described. The sequentially accomplished process comprises intermolecular Heck arylation of 2-vinyl imidazoles followed by an intramolecular aerobic oxidative C-H amination reaction promoted by the same Pd catalyst. This Pd-catalyzed tandem approach offers a straightforward protocol for the assembly of benzimidazo/phenanthroimidazo[1,2-a]quinolines in moderate to high yields, serving as a useful tool for the discovery of fluorescent materials.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c9ob00482cDOI Listing

Publication Analysis

Top Keywords

amination reaction
8
2-vinyl imidazoles
8
palladium-catalyzed tandem
4
tandem one-pot
4
one-pot synthesis
4
synthesis π-expanded
4
π-expanded imidazoles
4
imidazoles sequential
4
sequential heck
4
heck oxidative
4

Similar Publications

Chiral organic-inorganic metal halide (OIMH) materials are gaining increasing attention as candidates for asymmetric materials due to their unique photoelectric, chiral optic, and spintronic properties. The introduction of chirality into OIMHs is usually achieved by the use of chiral organic cations, while previous studies often focus on primary ammonium cations derived from commercially available chiral amines, limiting the tunability of the OIMH materials. Herein, we report the use of Zincke reactions to synthesize chiral N-substituted pyridinium salts, namely, (R)/(S)-methylbenzylpyridinium (/-MBnP) chloride and the corresponding 1D chiral OIMHs, (/-MBnP)PbX3 (X = Cl, Br, and I).

View Article and Find Full Text PDF

Heteroleptic (NHC/MIC) Biscarbene Ag(I) and Au(I) Complexes: Synthesis, Characterization and Catalytic Applications.

Chempluschem

January 2025

Universidad Autonoma del Estado de Hidalgo, Chemsitry, Carretera Pachuca-Tulancingo, Km 4.5, Mineral de la Reforma, 42090, Mineral de la Reforma, MEXICO.

A series of hetero-biscarbene silver(I) and gold(I) complexes of the general formula [NHC-M-MIC]PF6 (NHC = imidazol-2-ylidene, MIC = 1,2,3-triazol-5-ylidene) have been prepared via the treatment of NHC-M-Cl precursors in reaction with an in situ generated mesoionic carbene (MIC). The new heteroleptic complexes have been fully characterized including NMR spectroscopy, elemental analysis, melting points and single crystal X-ray diffraction. The silver(I) derivatives were employed successfully in the solvent free KA2 (ketone-alkyne-amine) coupling for the preparation of a series of quaternary carbon-containing propargyl amines while, the gold(I) biscarbenes, demonstrated a good performance in the A3 (aldehyde, amine, alkyne) coupling and the benzylic oxidation processes under low catalyst loadings.

View Article and Find Full Text PDF

N-glycosides exhibit diverse biological and pharmacological activities, making their efficient synthesis crucial for both biological research and drug development. Traditional acid-promoted N-glycosylation methods, which rely on the formation of oxocarbenium intermediates, often face significant challenges. These methods are water-sensitive and typically require neighboring group participation to achieve high selectivity.

View Article and Find Full Text PDF

The total synthesis of the stereoisomer of muanlactam predicted by DP4+ calculations, which differed from that reported for the natural product on the relative configuration at C19, was completed, and the structure of the polyenic macrolactam was fully confirmed. Construction of the stereocenters involved the iterative enantio- and diastereoselective Krische's allylation reaction for the formal -1,3-diol and the addition of a propargylic Grignard reagent to Ellman's chiral nonracemic -butylsulfinamide for the enantiopure amine fragment. The conjugated triene and diene units were constructed by Suzuki-Miyaura cross-coupling reactions of the corresponding alkenylboronates and alkenyl iodides.

View Article and Find Full Text PDF

Assembly of Biaryl Amines via Mild Copper-Catalyzed Coupling of Anilines with (Hetero)aryl Chlorides/Bromides.

Org Lett

January 2025

State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

CuI/6-hydroxy picolinohydrazide-catalyzed coupling of (hetero)aryl chlorides with anilines proceeded well at 100 °C to afford biaryl amines in a diverse manner, which represents the first example of Cu-catalyzed biaryl amines under milder conditions. The same catalytic system could make the coupling of (hetero)aryl bromides with anilines work at room temperature, giving the corresponding products with an excellent reaction scope.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!