23195-91-7

Upstream product

• 134305-25-2 cis-1-acetyl-3-styrylindole 
• 134305-26-3 (E)-1-(3-styryl-1H-indol-1-yl)ethanone 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 100-52-7 benzaldehyde 
• 487-89-8 Indole-3-carboxaldehyde 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 120-72-9 indole 
• 5153-67-3 nitrostyrene 
• 103-82-2 phenylacetic acid 
• 100-51-6 benzyl alcohol 
• 134305-24-1 1-phenyl-2-<3-(1-acetyl)indolyl>acrylic acid 
• 129271-97-2 1-(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate 
• 100-42-5 styrene 
• 144646-92-4 (E)-1-phenyl-2-(1-phenylsulfonylindol-3-yl)ethylene 

Relevant academic research and scientific papers

Antioxidant properties of ethenyl indole: DPPH assay and TDDFT studies

A series of ethenyl indoles (e.g.3-(4-substituted phenylethenyl-E)-N-H-indole) with various donor or acceptor substituents have been synthesized and their antioxidant properties have been studied. Ethenyl indoles exhibit antioxidant activity in a substituent dependent manner. Ethenyls bearing strong electron withdrawing substituents show weak or no antioxidant activity, whereas ethenyls with electron donating substituents exhibit antioxidant properties comparable to vitamin E. It can be seen from a plot of the percentage of inhibitionversusthe antioxidant concentration, that the hydroxy substituted ethenyl indole exhibits good antioxidant properties (50% inhibition concentration (IC50) ～ 24 μM) as compared to the other ethenyls (IC50: 30-63 μM) and that it is comparable to vitamin E (IC50～ 26 μM). The results are also supported by the computational data obtained through time dependent density functional theory (TDDFT) calculations. From the TDDFT and antioxidant study, it was shown that there is a correlation between the highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy, the ground state dipole moment, optical band gap, bond dissociation enthalpy and the ionization potential of the ethenyls with the antioxidant properties. A possible hydrogen and/or electron and proton transfer mechanism is suggested for the quenching of the free radical.

Visible-Light-Enabled Aerobic Denitrative C3-Alkenylation of Indoles with β-Nitrostyrenes

Herein, we unveil the first visible-light-mediated alkenylation reaction of indoles. The reaction follows a denitrative radical pathway where β-nitrostyrenes have been utilized as the alkene precursors for the C3-styrenylation of indoles under visible-light irradiation to afford biologically and synthetically important 3-alkenylindoles. High regioselectivity, absence of any photocatalyst, metal, external oxidant, acid or base, and the use of visible light and air as inexpensive clean reagents are the key highlights of the developed method.

Optical properties of 3-substituted indoles

The optical properties of various donor or acceptor p-phenyl substituted ethenyl indoles were studied in solvents of varying polarity using absorption, fluorescence and TDDFT methods. Ethenyl indole exhibits non-linear optical properties (NLO) in a substi

Chiral Imidodiphosphoric Acid-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Poly-Substituted 3,4-Dihydro-2 H-pyrans: [4 + 2] Cycloadditions of β,γ-Unsaturated α-Ketoesters and 3-Vinylindoles

Imidodiphosphoric acids were employed to catalyze inverse-electron-demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters and 3-vinylindoles. A series of optically active 3,4-dihydro-2H-pyran derivatives with three contiguous stereogenic centers was synthesized in excellent yields (70-99%), diastereoselectivities (>20:1), and enantioselectivities (73-99%). The resulting indole containing 3,4-dihydro-2H-pyran could be converted to tetrahydropyran derivatives, which appear in several biological active compounds by simple hydrogenation reduction.

C-H Alkenylation of Heteroarenes: Mechanism, Rate, and Selectivity Changes Enabled by Thioether Ligands

Thioether ancillary ligands have been identified that can greatly accelerate the C-H alkenylation of O-, S-, and N-heteroarenes. Kinetic data suggest thioether-Pd-catalyzed reactions can be as much as 800× faster than classic ligandless systems. Furthermore, mechanistic studies revealed C-H bond cleavage as the turnover-limiting step, and that rate acceleration upon thioether coordination is correlated to a change from a neutral to a cationic pathway for this key step. The formation of a cationic, low-coordinate catalytic intermediate in these reactions may also account for unusual catalyst-controlled site selectivity wherein C-H alkenylation of five-atom heteroarenes can occur under electronic control with thioether ligands even when this necessarily involves reaction at a more hindered C-H bond. The thioether effect also enables short reaction times under mild conditions for many O-, S-, and N-heteroarenes (55 examples), including examples of late-stage drug derivatization.

Copper-Catalyzed anti-Markovnikov Hydroindolation of Terminal Alkynes: Regioselective Synthesis of Bis(indolyl)alkanes

An efficient copper-catalyzed intermolecular hydroindolation reaction of terminal aryl alkynes to expeditiously synthesize bis(indolyl)alkanes in moderate to high yields is described. The double nucleophilic addition of two molecules of indole to one mole

Pd(II)-Catalyzed Ci-H Activation of Styrylindoles: Short, Efficient, and Regioselective Synthesis of Functionalized Carbazoles

A novel PdII-catalyzed approach for the direct synthesis of highly functionalized carbazoles from unprotected styrylindoles has been developed. The reaction features a variety of olefin substrates, which are readily switchable by subtle tuning

Aerobic C-H olefination of indoles via a cross-dehydrogenative coupling in continuous flow

Herein, we report the first site-selective, Pd(II)-catalyzed, cross-dehydrogenative Heck reaction of indoles in micro flow. By use of a capillary microreactor, we were able to boost the intrinsic kinetics to accelerate former hour-scale reaction condition

2-(1-benzotriazolyl)pyridine: A robust bidentate ligand for the palladium-catalyzed C-C (Suzuki, Heck, Fujiwara-Moritani, Sonogashira), C-N and C-S coupling reactions

A new class of bidentate ligand, 1-(pyridine-2-yl)-1H-benzo[d][1,2,3] triazole has been designed and employed for the palladium-catalyzed C-C (Suzuki, Heck, Fujiwara-Moritani, and Sonogashira), C-N and C-S coupling reactions. The ligand was found to be inexpensive, thermally stable, easy to synthesize from easily accessible starting materials on a multigram scale, show simplicity in use, and robustness in application, making this ligand effective for different coupling reactions. Suitably, the donor ability of the N=N bond of the benzotriazole ring and lone pair of electrons on the N of the pyridine ring enhance the bidentate ability of the ligand.

Palladium-catalyzed intermolecular C3 alkenylation of indoles using oxygen as the oxidant

A general and efficient palladium-catalyzed intermolecular direct C3 alkenylation of indoles using oxygen as the oxidant has been developed. The reaction is of complete regio- and stereoselectivity. All products are E-isomers at the C3-position, and no Z-