144688-69-7Relevant articles and documents
Paired Electrochemical Reactions and the On-Site Generation of a Chemical Reagent
Wu, Tiandi,Nguyen, Bichlien H.,Daugherty, Michael C.,Moeller, Kevin D.
, p. 3562 - 3565 (2019)
While the majority of reported paired electrochemical reactions involve carefully matched cathodic and anodic reactions, the precise matching of half reactions in an electrolysis cell is not generally necessary. During a constant current electrolysis almost any oxidation and reduction reaction can be paired, and in the presented work we capitalize on this observation by examining the coupling of anodic oxidation reactions with the production of hydrogen gas for use as a reagent in remote, Pd-catalyzed hydrogenation and hydrogenolysis reactions. To this end, an alcohol oxidation, an oxidative condensation, intramolecular anodic olefin coupling reactions, an amide oxidation, and a mediated oxidation were all shown to be compatible with the generation and use of hydrogen gas at the cathode. This pairing of an electrolysis reaction with the production of a chemical reagent or substrate has the potential to greatly expand the use of more energy efficient paired electrochemical reactions.
Expedient preparation of nazlinine and a small library of indole alkaloids using flow electrochemistry as an enabling technology
Kabeshov, Mikhail A.,Musio, Biagia,Murray, Philip R.D.,Browne, Duncan L.,Ley, Steven V.
supporting information, p. 4618 - 4621 (2015/01/08)
An expedient synthesis of the indole alkaloid nazlinine is reported. Judicious choice of flow electrochemistry as an enabling technology has permitted the rapid generation of a small library of unnatural relatives of this biologically active molecule. Furthermore, by conducting the key electrochemical Shono oxidation in a flow cell, the loading of electrolyte can be significantly reduced to 20 mol % while maintaining a stable, broadly applicable process.
Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis
Myers, Eddie L.,De Vries, Johannes G.,Aggarwal, Varinder K.
, p. 1893 - 1896 (2008/03/12)
(Chemical Equation Presented) All adducts one way: Iminium ions, generated in situ from the corresponding N,O-acetals, can be used as electrophiles in a Morita-Baylis-Hillman-type reaction with a wide range of Michael acceptors (enones, enals, S- and O-acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate).