1595283-06-9

Upstream product

• 2343-25-1 5-fluoro-2-amino-acetophenone 
• 100-58-3 phenylmagnesium bromide 
• 536-74-3 phenylacetylene 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 518058-72-5 methyl 5-fluoro-3-phenyl-1H-indole-2-carboxylate 
• 1259320-13-2 6-fluoro-4-phenyl-2-(trifluoromethyl)quinoline 
• 1196449-34-9 6-fluoro-2,4-diphenylquinoline 

Relevant academic research and scientific papers

Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines

Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).

PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions

A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is

Palladium(ii)-catalyzed vinylic geminal double C-H activation and alkyne annulation reaction: Synthesis of pentafulvenes

The first transition-metal-catalyzed vinylic geminal double C(sp2)-H activation and di-substituted alkyne annulation reaction is reported. This palladium(ii)-catalyzed, amide directed reaction of vinylic compounds with di-substituted alkynes offers an efficient synthetic path to pentafulvenes, which are very important compounds because of their bioactivity and interesting optical properties. A FeCl3-mediated transformation of pentafulvenes to fluorescent cyclopenta[b]quinolines is also developed.

Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines

A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.

Palladium-Catalyzed Phosphoryl-Carbamoylation of Alkenes: Construction of Nonbenzylic C(sp3)?P(O)R2 Bonds via C(sp3)?Pd(II)?P(O)R2 Reductive Elimination

We report the first example of palladium-catalyzed phosphoryl-carbamoylation of alkene-tethered carbamoyl chlorides with P(O)H compounds. Both H-phosphinates and secondary phosphine oxides are compatible with this reaction. DPE-Phos was used as ligand to facilitate nonbenzylic C(sp3)?P bonds formations via C(sp3)?Pd(II)?P reductive elimination. By using this protocol, a range of phosphorylated oxindoles and lactams were obtained in moderate to good yields. (Figure presented.).

Chemo- And Regioselective Magnesium-Catalyzed ortho-Alkenylation of Anilines

A simple and efficient catalytic system for a chemo- and regioselective ortho-alkenylation of anilines is presented. The new magnesium-catalyzed reaction allows the use of a wide range of alkynes and anilines with different electronic and steric propertie

Palladium-catalyzed cascade reactions of alkene-tethered carbamoyl chlorides with: N-tosyl hydrazones: Synthesis of alkene-functionalized oxindoles

A palladium-catalyzed cascade reaction of alkene-tethered carbamoyl chlorides with N-tosyl hydrazones is described. It provided a new way to synthesize various alkene-functionalized oxindoles bearing an all-carbon quaternary center. The olefin moieties co

Cleavage of C-C Bonds for the Synthesis of C2-Substituted Quinolines and Indoles by Catalyst-Controlled Tandem Annulation of 2-Vinylanilines and Alkynoates

The strategy for the synthesis of C2-substituted indoles and quinolines from 2-vinylanilines and alkynoates through C-C bond cleavage is developed. With these general methods, 2-substituted indoles and quinolines can be accessed via tandem Michael addition and cyclization with no requirement of oxidant. This strategy not only provides a method for the synthesis C2-substituted indoles in good yields through the simultaneous cleavage of C=C and C=C bonds under metal-free conditions but also provides a simple method for the generation of the C2-substituted quinolines in moderate yields via Pd-catalyzed C=C bond cleavage.

Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles

A copper-mediated intramolecular aza-Wacker-type cyclization was developed for the direct and efficient synthesis of 3-aryl indoles using 2-alkenylanilines in moderate to good yields with good functional group compatibility. This strategy shows the high efficiency, operational simplicity as well as broad substrate scope.

Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines

A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.