The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon–carbon bond formation via electrogenerated N-acyliminium ions
- Alan M. Jones and
- Craig E. Banks
Beilstein J. Org. Chem. 2014, 10, 3056–3072, doi:10.3762/bjoc.10.323
Graphical Abstract
Scheme 1: Application of anodic oxidation to the generation of new carbon-carbon bonds [11].
Scheme 2: The influence of the amino protecting group on the “kinetic” and “thermodynamic” anodic methoxylati...
Scheme 3: Example of the application of the cation pool method [17].
Scheme 4: A thiophenyl electroauxiliary allows for regioselective anodic oxidation [32].
Scheme 5: A diastereoselective cation carbohydroxylation reaction and postulated intermediate 18 [18].
Scheme 6: A radical addition and electron transfer reaction of N-acyliminium ions generated electrosynthetica...
Scheme 7: Catalytic indirect anodic fluorodesulfurization reaction [37].
Figure 1: Schematic of a cation flow system and also shown is the electrochemical microflow reactor reported ...
Figure 2: Example of a parallel laminar flow set-up. Figure redrawn from reference [38].
Figure 3: A catch and release cation pool method [42].
Scheme 8: Micromixing effects on yield 92% vs 36% and ratio of alkylation products [43].
Figure 4: Schematic illustration of the anodic substitution reaction system using acoustic emulsification. Fi...
Scheme 9: Electrooxidation to prepare a chiral oxidation mediator and application to the kinetic resolution o...
Scheme 10: Electrooxidation reactions on 4-membered ring systems [68].
Figure 5: Example of a chiral auxiliary Shono-oxidation intermediate [69].
Scheme 11: An electrochemical multicomponent reaction where a carbon felt anode and platinum cathode were util...
Scheme 12: Preparation of dienes using the Shono oxidation [23].
Scheme 13: Combination of an electroauxiliary mediated anodic oxidation and RCM to afford spirocyclic compound...
Scheme 14: Total synthesis of (+)-myrtine (66) using an electrochemical approach [78].
Scheme 15: Total synthesis of (−)-A58365A (70) and (±)-A58365B (71) [79].
Scheme 16: Anodic oxidation used in the preparation of the poison frog alkaloid 195C [80].
Scheme 17: Preparation of iminosugars using an electrochemical approach [81].
Scheme 18: The electrosynthetic preparation of α-L-fucosidase inhibitors [84,85].
Scheme 19: Enantioselective synthesis of the anaesthetic ropivacaine 85 [71].
Scheme 20: The preparation of synthetically challenging aza-nucleosides employing an electrochemical step [88].
Scheme 21: Synthesis of a bridged tricyclic diproline analogue 93 that induces α-helix conformation into linea...
Scheme 22: Synthesis of (i) a peptidomimetic and (ii) a functionalised peptide from silyl electroauxiliary pre...
Scheme 23: Examples of Phe7–Phe8 mimics prepared using an electrochemical approach [93].
Scheme 24: Preparation of arginine mimics employing an electrooxidation step [96].
Scheme 25: Preparation of chiral cyclic amino acids [20].
Scheme 26: Two-step preparation of Nazlinine 117 using Shono flow electrochemistry [101].
