13993-17-4Relevant articles and documents
A mild, efficient and improved protocol for the synthesis of novel indolyl crown ethers, di(indolyl)pyrazolyl methanes and 3-alkylated indoles using H 4[Si(W3O10)3]
Murugan, Rajendran,Karthikeyan, Murugesan,Perumal, Paramasivam T.,Reddy, Boreddy S.R.
, p. 12275 - 12281 (2005)
Efficient electrophilic substitution reactions of indoles with various aldehydes proceed smoothly in acetonitrile using heteropoly acid (H 4[Si(W3O10)3]) to afford the corresponding new indolyl crown ethers and
Ruthenium-Catalyzed Cascade Annulation of Indole with Propargyl Alcohols
Kaufmann, Julia,J?ckel, Elisabeth,Haak, Edgar
, p. 5908 - 5911 (2018)
Cascade transformations forming multiple bonds and one-pot procedures provide rapid access to natural-product-like scaffolds from simple precursors. These atom-economic processes are valuable tools in organic synthesis and drug discovery. Herein, we report on ruthenium-catalyzed cascade annulations of indole with readily available propargyl alcohols. These provide rapid access to diverse carbazoles, cyclohepta[b]indoles, and further fused polycycles with high selectivity. A bifunctional ruthenium complex featuring a redox-coupled cyclopentadienone ligand acts as a common catalyst for the different cascade processes.
Alkylation of Indoles with α,β-Unsaturated Ketones using Alumina in Hexanes
Zhang, Xiong,Jones-Mensah, Ebenezer,Deobald, Jackson,Magolan, Jakob
, p. 5548 - 5551 (2019/11/19)
We evaluated the influence of solvent on the alumina-promoted C3-alkylation of indoles with α,β-unsaturated ketones. We found that lipophilic solvents were generally superior to hydrophilic ones with hexanes offering the 3-alkyl indole products in high yields. Thus, we demonstrate an inexpensive and procedurally simple new process that pairs acidic alumina with hexanes to achieve this important Michael alkylation. The substrate scope includes twenty-four examples with reaction yields ranging from 61 to 96%. (Figure presented.).
Nickel-Catalyzed Coupling of Arylzinc Halides with Thioesters
Gehrtz, Paul H.,Kathe, Prasad,Fleischer, Ivana
supporting information, p. 8774 - 8778 (2018/06/26)
The Pd-catalyzed Fukuyama reaction of thioesters with organozinc reagents is a mild, functional-group-tolerant method for acylation chemistry. Its Ni-catalyzed variant might be a sustainable alternative to expensive catalytic Pd sources. We investigated the reaction of S-ethyl thioesters with aryl zinc halides with hetero- and homotopic Ni precatalysts and several ligands. The results show that both homo- and heterotopic species may contribute to catalysis. The substrate scope using an operationally homogeneous defined Ni complex was established. Acyl radicals are postulated as short-lived intermediates.
