Anti-Markovnikov hydroazidation of activated olefins via organic photoredox catalysis
Organic azides serve as synthetically useful surrogates for primary amines, a functional group which is ubiquitous in bioactive and medicinally relevant molecules. Historically, the formal hydroazidation of simple activated olefins and styrenes has proven
Nicewicz, David A.,Onuska, Nicholas P. R.,Rosario Collazo, José L.,Schutzbach-Horton, Megan E.
supporting information
p. 55 - 59
(2019/12/30)
Mechanistic aspects of aminium salt-catalyzed Diels-Alder reactions: The substrate ionization step
Substituent effects in the aminium salt catalyzed Diels-Alder reactions of 2,3-dimetnyl-1,3-butadiene with a series of meta and para substituted β-methylstyrenes are used to probe detailed mechanistic aspects of these reactions. Kinetic studies were carried out using two different aminium salt catalysts and also electrochemically, using anodic potentials corresponding to the oxidation potentials of the aminium salts. Substituent effects in the equilibrium oxidations of the styrene substrates to the corresponding cation radicals were also studied, via oxidation potential measurements. The results indicate rate determining one electron oxidation of the sytrenes to their cation radicals via an outer sphere electron transfer.
Yueh, Wang,Bauld, Nathan L.
p. 529 - 538
(2007/10/03)
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