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Search for "non-Kolbe oxidation" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

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

electroorganic techniques and future directions. Keywords: anodic oxidation; electrochemistry; electroorganic, electrosynthesis, N-acyliminium ions; natural products; non-Kolbe oxidation; peptidomimetics; Shono oxidation; synthesis; Review N-Acyliminium ions are synthetically versatile N-Acyliminium ions [1][2

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Scheme 1: Application of anodic oxidation to the generation of new carbon-carbon bonds [11].

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Scheme 2: The influence of the amino protecting group on the “kinetic” and “thermodynamic” anodic methoxylati...

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Scheme 3: Example of the application of the cation pool method [17].

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Scheme 4: A thiophenyl electroauxiliary allows for regioselective anodic oxidation [32].

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Scheme 5: A diastereoselective cation carbohydroxylation reaction and postulated intermediate 18 [18].

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Scheme 6: A radical addition and electron transfer reaction of N-acyliminium ions generated electrosynthetica...

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Scheme 7: Catalytic indirect anodic fluorodesulfurization reaction [37].

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Figure 1: Schematic of a cation flow system and also shown is the electrochemical microflow reactor reported ...

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Figure 2: Example of a parallel laminar flow set-up. Figure redrawn from reference [38].

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Figure 3: A catch and release cation pool method [42].

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Scheme 8: Micromixing effects on yield 92% vs 36% and ratio of alkylation products [43].

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Figure 4: Schematic illustration of the anodic substitution reaction system using acoustic emulsification. Fi...

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Scheme 9: Electrooxidation to prepare a chiral oxidation mediator and application to the kinetic resolution o...

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Scheme 10: Electrooxidation reactions on 4-membered ring systems [68].

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Figure 5: Example of a chiral auxiliary Shono-oxidation intermediate [69].

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Scheme 11: An electrochemical multicomponent reaction where a carbon felt anode and platinum cathode were util...

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Scheme 12: Preparation of dienes using the Shono oxidation [23].

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Scheme 13: Combination of an electroauxiliary mediated anodic oxidation and RCM to afford spirocyclic compound...

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Scheme 14: Total synthesis of (+)-myrtine (66) using an electrochemical approach [78].

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Scheme 15: Total synthesis of (−)-A58365A (70) and (±)-A58365B (71) [79].

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Scheme 16: Anodic oxidation used in the preparation of the poison frog alkaloid 195C [80].

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Scheme 17: Preparation of iminosugars using an electrochemical approach [81].

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Scheme 18: The electrosynthetic preparation of α-L-fucosidase inhibitors [84,85].

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Scheme 19: Enantioselective synthesis of the anaesthetic ropivacaine 85 [71].

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Scheme 20: The preparation of synthetically challenging aza-nucleosides employing an electrochemical step [88].

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Scheme 21: Synthesis of a bridged tricyclic diproline analogue 93 that induces α-helix conformation into linea...

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Scheme 22: Synthesis of (i) a peptidomimetic and (ii) a functionalised peptide from silyl electroauxiliary pre...

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Scheme 23: Examples of Phe⁷–Phe⁸ mimics prepared using an electrochemical approach [93].

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Scheme 24: Preparation of arginine mimics employing an electrooxidation step [96].

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Scheme 25: Preparation of chiral cyclic amino acids [20].

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Scheme 26: Two-step preparation of Nazlinine 117 using Shono flow electrochemistry [101].

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Review

Published 18 Dec 2014

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