78960-67-5Relevant academic research and scientific papers
Photodecarboxylative Amination of Redox-Active Esters with Diazirines
Maharaj, Vishala,Chandrachud, Preeti P.,Che, Wen,Wojtas, Lukasz,Lopchuk, Justin M.
supporting information, p. 8838 - 8842 (2021/11/24)
Diazirines have been recently demonstrated to serve as electrophilic amination reagents that afford diaziridines, versatile heterocycles that are readily transformed into amines, hydrazines, and nitrogen-containing heterocycles. Here, we report the photodecarboxylative amination of redox-active esters with diazirines using inexpensive photoactivators under mild conditions with an enhanced scope for primary substrates. The stability of diazirines to blue light is demonstrated, paving the way for further research into other photochemical amination methods with these unique heterocycles.
Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents
Chandrachud, Preeti P.,Wojtas, Lukasz,Lopchuk, Justin M.
supporting information, p. 21743 - 21750 (2021/01/11)
The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.
PROCESSES AND COMPOUNDS FOR THE DECARBOXYLATIVE AMINATION OF REDOX-ACTIVE ESTERS WITH DIAZIRINES
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Page/Page column 33; 34, (2020/12/30)
The invention described herein relates generally to processes for the synthesis of amine-containing organic compounds. More specifically, described herein relates to processes for the decarboxylative amination of redox-active esters with diazirines and the products formed thereof. Compounds for use in the above processes are also described.
Preparation of Perfluoroalkyl Ketones by the Reaction of Perfluoroalkyllithiums with Esters
Uno, Hidemitsu,Shiraishi, Yasukazu,Suzuki, Hitomi
, p. 2636 - 2642 (2007/10/02)
A variety of esters react with perfluoroalkyllithiums in situ generated from perfluoroalkyl iodides and methyllithium to give perfluoroalkyl ketones in good yields.Perfluoroalkyllithiums add to α,β-unsaturated esters only in the 1,2-addition mode even in the presence of copper salt.Exception was observed in the reaction with maleates where perfluoroalkylated succinic esters and normal 1,2-addition products are obtained in comparable amounts.
Oxidation of Fluoroalkyl-Substituted Carbinols by the Dess-Martin Reagent
Linderman, Russell J.,Graves, David M.
, p. 661 - 668 (2007/10/02)
The efficient oxidation of mono-, di-, tri-, and perfluoroalkyl-substituted carbinols has been accommplished by the Dess-Martin periodinane oxidant.A variety of functional groups are compatible with the oxidation procedure.Monitoring the oxidation by 19F NMR indicated that a discreet periodinane intermediate is formed during the course of the reaction.Nonnucleophilic or sterically encumbered α-thiofluoro carbinols were readily oxidized; however, a nucleophilic α-thio-substituted trifluoromethyl carbinol was not.A tert-butyl alcohol modified periodinane oxidant was ultimately employed to achieve oxidation in this example.
An Efficient Synthesis of Perfluoroalkyl Ketones Using Perfluoroalkyllithiums
Uno, Hidemitsu,Shiraishi, Yasukazu,Simokawa, Kazuhiro,Suzuki, Hitomi
, p. 1153 - 1156 (2007/10/02)
Perfluoroalkylation of esters with perfluoroalkyllithiums occurs smoothly in ether at -78 deg C, giving the corresponding perfluoroalkyl ketones in good yields.
