23073-17-8

Upstream product

• 64-17-5 ethanol 
• 758640-21-0 N-Benzylaniline 
• 70-11-1 α-bromoacetophenone 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 71687-81-5 N-benzyl-2-bromoaniline 
• 98018-66-7 N-benzyl-2-chloroaniline 
• 871506-88-6 1-benzyl-2,2-diphenyl-3-fluoroaziridine 
• 96-09-3 styrene oxide 
• 614-31-3 N-benzyl-N-phenylhydrazine 
• 36810-78-3 2-(benzyl(phenyl)amino)-1-phenylethan-1-one 
• 1504-16-1 3-phenyl-1H-indole 
• 100-39-0 benzyl bromide 
• 3377-71-7 N-benzylindole 
• 479675-59-7 (E)-1-phenylethan-1-one O-perfluorobenzoyl oxime 

Downstream Products

• 1504-16-1 3-phenyl-1H-indole 

Relevant academic research and scientific papers

Fluoroaziridines as novel substrates in the modified Petasis reaction: synthesis of monofluorinated propargyl amines

Reaction of 2-fluoroaziridines with potassium alkynyltrifluoroborates in the presence of BF3·OEt2 leads to fluorinated propargyl amines in moderate to good yields. The reaction proceeds as an in situ isomerization of 2-fluoroaziridin

C3-Arylation of indoles with aryl ketonesviaC-C/C-H activations

C3-Arylation of indoles with aryl ketones is accomplishedviapalladium-catalyzed ligand-promoted Ar-C(O) cleavage and subsequent C-H arylation of indole. Various (hetero)aryl ketones are compatible in this reaction, affording the corresponding 3-arylindoles in moderate to good yields. Further introduction of an indole moiety into the natural products desoxyestrone and evodiamine demonstrate the synthetic utility of this protocol.

Arylation of indoles using cyclohexanones dually-catalyzed by niobic acid and palladium-on-carbons

3-Arylindoles were easily constructed from indoles and cyclohexanone derivatives using a combination of catalytic niobic acid-on-carbon (Nb2O5/C) and palladium-on-carbon (Pd/C) under heating conditions without any oxidants. The Lewis acidic Nb2O5/C promoted the nucleophilic addition of indoles to the cyclohexanones, and the subsequent dehydration and Pd/C-catalyzed dehydrogenation produced the 3-arylindoles. The additive 2,3-dimethyl-1,3-butadiene worked as a hydrogen acceptor to facilitate the dehydrogenation step.

Catalytic Au(i)/Au(iii) arylation with the hemilabile MeDalphos ligand: Unusual selectivity for electron-rich iodoarenes and efficient application to indoles

The ability of the hemilabile (P,N) MeDalphos ligand to trigger oxidative addition of iodoarenes to gold has been thoroughly studied. Competition experiments and Hammett correlations substantiate a clear preference of gold for electron-enriched substrates both in stoichiometric oxidative addition reactions and in catalytic C-C cross-coupling with 1,3,5-trimethoxybenzene. This feature markedly contrasts with the higher reactivity of electron-deprived substrates typically encountered with palladium. Based on DFT calculations and detailed analysis of the key transition states (using NBO, CDA and ETS-NOCV methods in particular), the different behavior of the two metals is proposed to result from inverse electron flow between the substrate and metal. Indeed, oxidative addition of iodobenzene is associated with a charge transfer from the substrate to the metal at the transition state for gold, but opposite for palladium. The higher electrophilicity of the gold center favors electron-rich substrates while important back-donation from palladium favors electron-poor substrates. Facile oxidative addition of iodoarenes combined with the propensity of gold(iii) complexes to readily react with electron-rich (hetero)arenes prompted us to apply the (MeDalphos)AuCl complex in the catalytic arylation of indoles, a challenging but very important transformation. The gold complex proved to be very efficient, general and robust. It displays complete regioselectivity for C3 arylation, it tolerates a variety of functional groups at both the iodoarene and indole partners (NO2, CO2Me, Br, OTf, Bpin, OMe?) and it proceeds under mild conditions (75 °C, 2 h).

Divergent Functionalization of N-Alkyl-2-alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines

An efficient divergent functionalization of N-alkylated ortho-alkenylanilines to substituted indoles and quinolines has been accomplished by employing rhodium-catalyzed cross-dehydrogenative coupling and silver-mediated oxidative cyclization, respectively. The developed methods tolerate various functional groups and allow the synthesis of substituted indoles and quinolines in good to excellent yield. Synthetic utility is demonstrated through conversion to an indole with antimicrobial activity and C?H bond functionalization of 2-arylquinolines. Furthermore, a plausible mechanism was proposed based on preliminary mechanistic investigations.

Electronic effect of substituents on anilines favors 1,4-addition to: Trans -β-nitrostyrenes: Access to N -substituted 3-arylindoles and 3-arylindoles

A simple and an efficient method for the regioselective synthesis of N-alkyl/aryl/H 3-arylindole derivatives from N-substituted anilines and trans-β-nitrostyrenes has been described using 10 mol% of bismuth(iii) triflate as a catalyst in acetonitrile at 80 °C. The present protocol profits from the formation of new C-C and C-N bonds, broad substrate scope and moderate to good yields.

Electron-Transfer and Hydride-Transfer Pathways in the Stoltz–Grubbs Reducing System (KOtBu/Et3SiH)

Recent studies by Stoltz, Grubbs et al. have shown that triethylsilane and potassium tert-butoxide react to form a highly attractive and versatile system that shows (reversible) silylation of arenes and heteroarenes as well as reductive cleavage of C?O bonds in aryl ethers and C?S bonds in aryl thioethers. Their extensive mechanistic studies indicate a complex network of reactions with a number of possible intermediates and mechanisms, but their reactions likely feature silyl radicals undergoing addition reactions and SH2 reactions. This paper focuses on the same system, but through computational and experimental studies, reports complementary facets of its chemistry based on a) single-electron transfer (SET), and b) hydride delivery reactions to arenes.

Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides

We report an unprecedented transition metal-free coupling of indoles with aryl halides. The reaction is promoted by KOtBu and is regioselective for C3 over N. The use of degassed solvents devoid of oxygen is necessary for the success of the transformation. Preliminary studies implicate a hybrid mechanism that involves both aryne intermediates and non-propagative radical processes. Electron transfer is also a distinct possibility. These conclusions were substantiated by EPR data, isotopic labeling studies, and the use of radical scavengers and electron transfer inhibitors.

Cobalt(III)-Catalyzed Intramolecular Cross-Dehydrogenative C?H/X?H Coupling: Efficient Synthesis of Indoles and Benzofurans

An efficient cobalt(III)-catalyzed intramolecular cross-dehydrogenative C?H/N?H coupling of ortho-alkenylanilines has been developed utilizing O2as a terminal oxidant. The developed reaction tolerates various reactive functional groups and allo

NH4PF6-promoted cyclodehydration of α-amino carbonyl compounds: Efficient synthesis of pyrrolo[3,2,1-ij]quinoline and indole derivatives

NH4PF6 is an inexpensive, safe, and low-toxicity inorganic salt; it was found to promote the cyclodehydration of α-amino carbonyl compounds in the absence of metal reagents. This simple cyclodehydration strategy enables highly atom-e