3336-00-3

Upstream product

• 3335-97-5 1-methyl-3-phenylindolin-2-one 
• 620-05-3 iodomethylbenzene 
• 19078-72-9 bromo(phenyl)acetyl chloride 
• 66003-76-7 Diphenyliodonium triflate 
• 98-80-6 phenylboronic acid 
• 91-56-5 indole-2,3-dione 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 108-88-3 toluene 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 61-70-1 N-methyl-2-indolinone 
• 100-39-0 benzyl bromide 
• 62-53-3 aniline 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 1610460-71-3 C₂₂H₁₉NO 

Relevant academic research and scientific papers

Palladium-Catalyzed Chemoselective Activation of sp3 vs sp2 C-H Bonds: Oxidative Coupling to Form Quaternary Centers

The oxidative activation of alkyl C-H bonds vs arene C-H bonds with Pd(OAc)2 has been found to be generalizable to a number of nucleophilic substrates, allowing the formation of a range of hindered quaternary centers. The substrates share a common mechanistic path wherein Pd(II) initiates an oxidative dimerization. The resultant dimer modifies the palladium catalyst to favor activation of alkyl C-H bonds, in contrast to the trends typically observed via a concerted metalation-deprotonation mechanism. Notably, insertion occurs at the terminus of the alkyl arene for hindered substrates. Two different oxidant systems were discovered that turn over the process. Parameters have been identified that predict which substrates are productive in this reaction.

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.

Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles

The first nickel-catalyzed domino Heck cyclization/Suzuki coupling reaction for the synthesis of 3,3-disubstituted oxindoles bearing quaternary all-carbon centers is reported. A wide range of electrophiles, such as aryl iodides, bromides, triflates, and c

Copper(I)-catalyzed aryl or vinyl addition to electron-deficient alkenes cascaded by cationic cyclization

An exoselective copper-catalyzed arylation- and vinylation-carbocyclization of electron-deficient alkenes was developed to provide rapid and efficient access to a variety of functionalized 3,3-disubstituted oxindoles. With this method, a highly efficient and concise formal synthesis of (±)- physostigmine and (±)-physovenine has been completed.

Copper-catalyzed bis-arylations of alkenes leading to oxindole derivatives

A simple and practical copper-catalyzed approach to oxindole derivatives by copper-catalyzed bis-arylation of N-alkyl-N-phenylacrylamides with diaryliodonium triflates has been developed under mild conditions, and the method is of tolerance towards some functional groups in the substrates. This journal is the Partner Organisations 2014.

LCopper-catalyzed diarylation of activated alkenes with diaryliodonium salts

Cu(OTf)2-catalyzed diarylation of activated alkenes by using diaryliodonium(III) salts has been developed. With this method, arylated oxindoles can be easily accessed in good yields. Insights into the mechanism of copper-catalyzed arylations are discussed, and the findings are expected to help increase the level of understanding of catalytic arylations with diaryliodonium salts. Georg Thieme Verlag Stuttgart. New York.

Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols: Synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones

2-Alkylaminophenylprop-1-yn-3-ols, prepared from the lithium diisopropylamide (LDA)- mediated 1,2-addition of alkynes to 1-(2-aminophenyl) ketones, can be converted to 3,3-disubstituted 2-oxindoles by using silica gel in n-hexane/ ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale-up strategy for the synthesis of 2-oxindoles was exemplified by the large-scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.

Oxindole synthesis by direct coupling of Csp2-H and C sp3-H centers

(Chemical Equation Presented) An sp2/sp3 get-together: A novel and efficient method can be used to synthesize 3,3-disubstitued oxindoles by the direct intramolecular oxidative coupling of an aryl Csp2-H and a Csp3-H center (see scheme; DMF = N,N-dimethylformamide).