42773-95-5

Upstream product

• 55875-34-8 2-phenyl-propionic acid-(N'-methyl-N'-phenyl-hydrazide) 
• 67-64-1 acetone 
• 105464-53-7 N-methyl-2,N-diphenylpropionamide 
• 1164334-38-6 N-(2-chlorophenyl)-N-methyl-2-phenylpropanoic acid amide 
• 24438-17-3 1,3-dimethylindolin-2-one 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 91-56-5 indole-2,3-dione 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 61-70-1 N-methyl-2-indolinone 
• 74-83-9 methyl bromide 
• 3335-97-5 1-methyl-3-phenylindolin-2-one 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Synthesis and Reactivity of Model Intermediates Proposed for the Pd-Catalyzed Remote C-H Functionalization of N-(2-Haloaryl)acrylamides

We have studied the possible reaction pathways operating in the Pd-catalyzed remote C-H functionalization of N-(2-haloaryl)acrylamides from an organometallic approach. We have isolated and characterized several proposed reaction intermediates, such as σ-a

Transition-metal-free α-arylation of oxindoles: Vi a visible-light-promoted electron transfer

An operationally simple photochemical strategy for the direct arylation of oxindoles with (hetero)aryl halides in the absence of both transition metals and photoredox catalysts has been developed. The reaction provides an efficient way to construct various 3-aryloxindole building blocks of pharmaceutical interest at ambient temperature by using household compact fluorescent light (CFL) bulbs as the light source. Preliminarily, mechanistic studies revealed that the intermolecular electron transfer relied on the formation of photon-absorbing electron-donor-acceptor (EDA) complexes between electron-rich oxindole enolates and electron-deficient (hetero)aryl halides, and a radical chain mechanism was operative.

DMF-Promoted Redox-Neutral Ni-Catalyzed Intramolecular Hydroarylation of Alkene with Simple Arene

A redox-neutral Ni-catalyzed intramolecular hydroarylation of alkene with simple arene has been developed, in which DMF played a proton shuttle role in facilitating the intramolecular coupling, avoiding the use of additional reductants and oxidants. A series of oxindoles with a quaternary center were obtained in up to 99% yield.

Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles

Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.

Rhodium-Catalyzed Enantioselective Reductive Arylation: Convenient Access to 3,3-Disubstituted Oxindoles

A rhodium-Josiphos(L*) catalyzed enantioselective intramolecular hydroarylation reaction is described. The reductive cyclization of o-bromoaniline-derived acrylamides provides convenient access to 3,3-disubstituted oxindoles in good yields and with excell

Metal alkylidene complexes comprising an unsymmetrical unsaturated NHC ligand

The present invention relates to metal alkylidene complex comprising a 1-aryl-3-alkyl-imidazol-2-ylidene ligand, wherein the aryl group of said 1-aryl-3-alkyl-imidazol-2-ylidene ligand is an aromatic and wherein the alkyl group of said 1-aryl-3-alkyl-imidazol-2-ylidene ligand is selected from the group consisting of a cyclic secondary aliphatic alkyl and a C2-C10-heteroalkyl, and wherein said metal is selected from the group consisting of Pd, Ag, Au, Ir, Rh, Cu, Ni, Mg, Zn, Ti, Pt and Fe, with the provision that the aryl group of said 1-aryl-3-alkyl-imidazol-2-ylidene ligand is other than an ortho-hydroxyaryl group when said metal is Pd and when said cyclic secondary aliphatic alkyl is cyclohexyl.

Domino Heck/borylation sequence towards indolinone-3-methyl boronic esters: trapping of the σ-alkylpalladium intermediate with boron

Pd-catalyzed domino Heck/borylation of acrylamides with B2pin2 is reported to generate synthetically useful indolinone-3-methyl boronic esters, via capturing σ-alkyl palladium with boron. Further functionalization of the obtained boronic ester qualify it as a new starting point for the functionalization of specific C(sp3)-H bond. Moreover, the application of an Ugi-adduct as starting material or B2nep2 as an alternative boron source works equally well, making this a broadly applicable and robust method for the formation of a C-C and C-B bond in a single operation.

Copper(ii) chloride mediated (aza)oxindole synthesis by oxidative coupling of Csp2-H and Csp3-H centers: Substrate scope and DFT study

A CuCl2 mediated direct intramolecular oxidative coupling of Csp2-H and Csp3-H centers gives access to 3,3-disubstituted oxindoles containing aromatic, heteroaromatic and alkyl substituents as well as a heteroatom at the quaternary center in good to excellent yields. The reaction is carried out in the presence of NaOtBu and CuCl2 in DMF at 110 °C. The key step of this reaction is the formation of an amidyl radical by one electron oxidation of amide enolate followed by an intramolecular radical cyclization reaction (homolytic aromatic substitution reaction). A detailed DFT study shows that the cyclization of the amidyl radical is the rate-limiting step in the oxindole synthesis, whereas the second single electron transfer (SET) becomes the rate-determining step in the aza-oxindole formation. Computational data are in agreement with the experimentally observed relative reactivity and regioselectivity.

Transition-metal-free synthesis of oxindoles by potassium tert-butoxide-promoted intramolecular α-arylation

Potassium tert-butoxide-mediated intramolecular α-arylations of fluoro- and chloro-substituted anilides provide oxindoles in DMF at 80 °C. In this manner, diversely substituted products have been obtained in moderate to high yields.