108545-66-0

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 1086975-14-5 potassium 4-cyanophenethyltrifluoroborate 
• 3058-39-7 4-iodobenzonitrile 
• 75400-50-9 9-[2-(4-methoxy-phenyl)-ethyl]-9-bora-bicyclo[3.3.1]nonane 
• 637-69-4 4-Methoxystyrene 
• 104-85-8 para-methylbenzonitrile 
• 824-94-2 p-methoxybenzyl chloride 
• 623-03-0 4-Cyanochlorobenzene 

Relevant academic research and scientific papers

Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study

The rearrangement of sulfamoyl azides under thermal conditions to form a C-C bond while breaking two C-N bonds is reported. Mechanistic study shows that this reaction goes through a Curtius-type rearrangement to form a 1,1-diazene, then which rearranges possibly through both a concerted rearrangement process and a stepwise radical process. This rearrangement could be used in the synthesis of complex biologically active molecules, such as sterols, and piperine derivatives.

The copper-catalysed Suzuki-Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation

We report the first example of CuI-catalysed coupling of alkylboron reagents with aryl and heteroaryl iodides that affords products in good to excellent yields. Preliminary mechanistic studies with alkylborates indicate that the anionic (alkoxy)(alkyl)borates, generated from alkyllithium and alkoxyboron reagents, undergo disproportionation to anionic dialkylborates and that both anionic alkylborates are active for transmetalation to a CuI-catalyst. Results from a radical clock experiment and the Hammett plot imply that the reaction likely proceeds via a non-radical pathway.

Utilization of potassium vinyltrifluoroborate in the development of a 1,2-dianion equivalent

Previous studies of orthogonally reactive dibora species led to the discovery of a unique reactivity pattern associated with potassium vinyltrifluoroborate. Upon hydroboration, the vinyltrifluoroborate generates a 1,2-diboraethane, which is distinct from

Aryl Radicals from Electrochemical Reduction of Aryl Halides. Addition on Olefins

Aryl radicals generated by direct and indirect (by means of an aromatic anion radical mediator) electrochemistry are reacted with olefins in liquid ammonia and in organic solvents (Me2SO, MeCN, DMF).The arylated product is obtained in good yield in the latter case.In pure liquid NH3, the yields are extremely poor.They are improved upon addition of a proton donor such as urea or water; further increase of yields is obtained upon addition of 2-propanol.A reaction mechanism is proposed based on these observations and on the results of deuterium incorporation experiments.Cyclic voltammetry is used to determine the rate constant of the key step in the mechanism, viz, the addition of the aryl radical to the olefin, through its competition with its reaction with nucleophiles in the framework of an SRN1 substitution process.

ADDITION OF ARYL RADICALS GENERATED FROM ELECTROCHEMICAL REDUCTION OF ARYL HALIDES ON CARBON-CARBON DOUBLE BONDS.

Aryl radicals generated by electrochemical reduction of aryl halides in aprotic medium react with styrene and its derivatives to give arylated addition compounds.