1287759-88-9

Upstream product

• 88320-94-9 2-benzylpropenoyl chloride 
• 62-53-3 aniline 
• 1353568-88-3 2-(methoxymethyl)-N-methyl-N-phenylacrylamide 
• 98-80-6 phenylboronic acid 
• 74-88-4 methyl iodide 
• 5669-19-2 2-Benzyl-2-propenoic acid 
• 100-61-8 N-methylaniline 

Downstream Products

• 1403475-42-2 C₁₇H₁₅Br₂NO 
• 1449117-14-9 3-(azidomethyl)-3-benzyl-1-methylindolin-2-one 
• 1558025-41-4 3-benzyl-1-methyl-3-(((trifluoromethyl)thio)methyl)indolin-2-one 
• 32380-61-3 3,3-dibenzyl-1-methylindolin-2-one 
• 3389-80-8 3-(3-benzyl-1-methyl-2-oxoindolin-3-yl)propanenitrile 

Relevant academic research and scientific papers

Synthesis method of allyl aryl compound

The invention belongs to the technical field of synthesis of organic compounds, and relates to a synthesis method of an allyl aryl compound. Under the action of a nickel catalyst and a ligand, a cross-coupling reaction of an allyl alkyl ether compound and an arylboronic acid reagent is carried out, activation of carbon-oxygen bonds is realized, and the allyl aryl compound is obtained. The method has the advantages of low cost, simple process, high product purity and yield, wide substrate application range and the like. The synthesis method can be used for modifying drug molecules, and the synthesized product can be used as a novel medical intermediate.

Nickel-Catalyzed Arylation of C(sp3)-O Bonds in Allylic Alkyl Ethers with Organoboron Compounds

A nickel-catalyzed cross-coupling of allylic alkyl ethers with organoboron compounds through the cleavage of the inert C(sp3)-O(alkyl) bonds is described. Several types of allylic alkyl ethers can be coupled with various boronic acids or their derivatives to give the corresponding products in good to excellent yields with wide functional group tolerance and excellent regioselectivity. The gram-scale reaction and late-stage modification of biologically active compounds further prove the practicality of this synthetic method.

Nontraditional Application of the Photo-Fenton Process: A Novel Strategy for Molecular Construction Using Formamide and Flow Chemistry

Instead of destroying organic compounds, for the first time the photo-Fenton reaction was employed to construct them. Oxindole and spiro-oxindole scaffolds, which are frequently found in natural products, were selected as molecular targets. The development of a photochemical flow reactor employing the photo-Fenton reaction in formamide resulted in an excellent synthetic methodology for oxindoles. Non-anhydrous conditions are required, and readily available chemicals and mild conditions are employed. Also, novel synthetic approaches for new spiro compounds were efficiently developed using functionalized oxindoles as key intermediates.

Nickel-Catalyzed Transformation of Diazoacetates to Alkyl Radicals Using Alcohol as a Hydrogen Source

A nickel-catalyzed transformation of diazoacetates to α-carbonyl methylene radicals has been disclosed in the presence of hyperoxide using ethanol as a hydrogen source and solvent. This strategy is successfully applied in the formation of indolin-2-ones or 1,4-dicarbonyl compounds from acrylamides or enamides in moderate to good yields. These reactions undergo radical addition onto C-C double bonds followed by a cyclization/oxidation or an oxidation/hydrolysis process, respectively.

UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions

UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.

Oxidant-Free Rhodium(I)-Catalyzed Difunctionalization of Acrylamide: An Efficient Approach to Synthesize Oxindoles

(Figure Presented) The first rhodium(I)-catalyzed difunctionalization of arylacrylamides to synthesize oxindoles is developed, and it does not require the assistance of an oxidant. This method provides an efficient approach to generate various useful functionalized oxindoles, some of which cannot be easily accessed by previous approaches.

Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the Synthesis of Pyrazoline-Functionalized Oxindoles

An efficient and practical tandem cyclization/addition/cyclization strategy is developed for the initial generated hydrazonyl radicals derived from the oxidation of β,γ-unsaturated hydrazones. By using this protocol, structurally novel pyrazoline-functionalized oxindoles are prepared by the reaction of easily accessible β,γ-unsaturated hydrazones with N-aryl acrylamides under the metal- and solvent-free conditions of DTBP (di-tert-butyl peroxide) via a tandem intra/intermolecular C-N/C-C/C-C bond formation.

Arylnitration of alkenes by nitration/C-H functionalization cascade using AgNO3 and HOAc

A novel arylnitration of alkenes by nitration and C-H functionalization cascade process has been developed. This methodology provides an efficient way to construct a variety of nitro-containing oxindoles and dihydroquinolin-2(1H)- ones. In addition, the process exhibits significant functional group tolerance. Moreover, the use of inexpensive and readily available starting materials makes this practical and atom-economical approach particularly attractive.

Synthesis of oxindoles through silver-catalyzed trifluoromethylation-, difluoromethylation- and arylsulfonylation-cyclization reaction of N-arylacrylamides

Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced. Copyright

Arylnitration of alkenes by nitration/C-H functionalization cascade using AgNO3 and HOAc

A novel arylnitration of alkenes by nitration and C-H functionalization cascade process has been developed. This methodology provides an efficient way to construct a variety of nitro-containing oxindoles and dihydroquinolin-2(1H)-ones. In addition, the process exhibits significant functional group tolerance. Moreover, the use of inexpensive and readily available starting materials makes this practical and atom-economical approach particularly attractive.