98583-80-3

Upstream product

• 20769-85-1 2-bromoisobutyric acid bromide 
• 100-61-8 N-methylaniline 
• 55577-65-6 2,N-dimethyl-N-phenylpropanamide 
• 15796-89-1 N-methyl-N-phenylmethacrylamide 

Downstream Products

• 15796-89-1 N-methyl-N-phenylmethacrylamide 
• 108-95-2 phenol 
• 20200-86-6 1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one 
• 55577-65-6 2,N-dimethyl-N-phenylpropanamide 
• 31883-80-4 3,4-dihydro-1,3-dimethylquinolin-2(1H)-one 
• 100134-55-2 2-cyano-N,2-dimethyl-N-phenylpropanamide 
• 647018-71-1 (1-{tert-butyl-[1-methyl-1-(methyl-phenyl-carbamoyl)-ethoxy]-amino}-2,2-dimethyl-propyl)-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Hydroarylation of Activated Alkenes Enabled by Proton-Coupled Electron Transfer

Hydroarylation of alkenes has been demonstrated to be an atom-economic approach to access functionalized arenes from easily accessible raw materials. Herein, we report a visible light-induced photocatalytic system that enables intramolecular hydroarylation of N-arylacrylamides with high 5-exo-trig selectivity through robust proton-coupled electron transfer (PCET). This mild hydroarylation protocol provides a straightforward entry to structurally valuable oxindoles and complements previously established 6-endo-trig cyclization by photochemical triplet energy transfer (TET).

Access to α-Cyano Carbonyls Bearing a Quaternary Carbon Center by Reductive Cyanation

Reductive cyanation of tertiary alkyl bromides using electrophilic cyanating reagent and zinc reductant was developed, providing various α-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center in good to excellent yields under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.

Visible-Light-Driven Aryl Migration and Cyclization of α-Azido Amides

This paper reports two new visible-light-promoted radical reactions of α-azido amides. By catalysis of [Ir(ppy)2(dtbbpy)]PF6 with i-Pr2NEt as the reducing agent, N-aryl α-azido tertiary amides were first converted to the corresponding aminyl radicals through reduction of the azido group; the aminyl radicals then underwent N-to-N aryl migration to give α-anilinyl-functionalized amides. α-Azido secondary amides, on the other hand, reacted with the solvent ethanol and i-Pr2NEt to afford the imidazolinone products.

Copper-Salt-Promoted Carbocyclization Reactions of α-Bromo- N -arylacylamides

A mild and convenient synthetic method for oxindoles and α-arylacylamides bearing an all carbon quaternary stereocenter from the readily available α-bromo-N-arylacylamides has been developed. This Cu(acac)2/Phen-promoted radical cyclization rea

Alkoxyamine-Mediated Radical Synthesis of Indolinones and Indolines

(Equation presented) Thermolysis of α-alkoxyamino propionanilides produces indolinones, whereas thermal reaction of N-allylaniline derivatives with various Tordo-type alkoxyamines results in formation of indolines in the radical regime.

Tandem Radical Translocation and Homolytic Aromatic Substitution: a Convenient and Efficient Route to Oxindoles

Suitable o-bromo-N-methylanilides are efficiently converted into oxindoles by treatment with tributylstannane at 160 degC via tandem translocation of the initially formed aryl radical and intramolecular homolytic substitution.