Ozone-Mediated Amine Oxidation and Beyond: A Solvent-Free, Flow-Chemistry Approach

Author(s):  
Eric A. Skrotzki ◽  
Jaya Kishore Vandavasi ◽  
Stephen G. Newman
2021 ◽  
Author(s):  
Eric Skrotzki ◽  
Jaya Kishore Vandavasi ◽  
Stephen Newman

Ozone is a powerful oxidant, most commonly used for oxidation of alkenes to carbonyls. The synthetic utility of other ozone-mediated reactions is hindered by its high reactivity and propensity to over-oxidize organic molecules, including most solvents. This challenge can largely be mitigated by adsorbing both substrate and ozone onto silica gel, providing a solvent-free oxidation method. In this manuscript, a flow-based packed bed reactor approach is described that provides exceptional control of reaction temperature and time of this reaction to achieve improved control and chemoselectivity over this challenging reaction. A powerful method to oxidize primary amines into nitroalkanes is achieved. Examples of pyridine, C–H bond, and arene oxidations are also demonstrated, confirming the system is generalizable to diverse ozone-mediated processes.<br>


2021 ◽  
Author(s):  
Eric Skrotzki ◽  
Jaya Kishore Vandavasi ◽  
Stephen Newman

Ozone is a powerful oxidant, most commonly used for oxidation of alkenes to carbonyls. The synthetic utility of other ozone-mediated reactions is hindered by its high reactivity and propensity to over-oxidize organic molecules, including most solvents. This challenge can largely be mitigated by adsorbing both substrate and ozone onto silica gel, providing a solvent-free oxidation method. In this manuscript, a flow-based packed bed reactor approach is described that provides exceptional control of reaction temperature and time of this reaction to achieve improved control and chemoselectivity over this challenging reaction. A powerful method to oxidize primary amines into nitroalkanes is achieved. Examples of pyridine, C–H bond, and arene oxidations are also demonstrated, confirming the system is generalizable to diverse ozone-mediated processes.<br>


Author(s):  
Nirvik Sen ◽  
K.K. Singh ◽  
S. Mukhopadhyay ◽  
K.T. Shenoy

2016 ◽  
Vol 20 (12) ◽  
pp. 2043-2049 ◽  
Author(s):  
Michael J. Pedersen ◽  
Tommy Skovby ◽  
Michael J. Mealy ◽  
Kim Dam-Johansen ◽  
Søren Kiil

2000 ◽  
Vol 24 (6) ◽  
pp. iii-iii
Author(s):  
Natasha V. Raikhel ◽  
Mikio Nishimura ◽  
Ralph S. Quatrano ◽  
Stephen H. Howell ◽  
William Davies ◽  
...  
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2020 ◽  
Author(s):  
Marta Antoniv ◽  
Shitong Zhu ◽  
Sehoon Chang ◽  
Nouf AlJabri
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1995 ◽  
Vol 95 (3) ◽  
pp. 399-408 ◽  
Author(s):  
Elena Toll ◽  
Federico J. Castillo ◽  
Pierre Crespi ◽  
Michele Crevecoeur ◽  
Hubert Greppin

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