The direct synthetic organic use of electricity is currently experiencing a renaissance. More synthetically oriented laboratories working in this area are exploiting both novel and more traditional concepts, paving the way to broader applications of this niche technology. As only electrons serve as reagents, the generation of reagent waste is efficiently avoided. Moreover, stoichiometric reagents can be regenerated and allow a transformation to be conducted in an electrocatalytic fashion. However, the application of electroorganic transformations is more than minimizing the waste footprint, it rather gives rise to inherently safe processes, reduces the number of steps of many syntheses, allows for milder reaction conditions, provides alternative means to access desired structural entities, and creates intellectual property (IP) space. When the electricity originates from renewable resources, this surplus might be directly employed as a terminal oxidizing or reducing agent, providing an ultra-sustainable and therefore highly attractive technique. This Review surveys recent developments in electrochemical synthesis that will influence the future of this area.

Electrifying Organic Synthesis

Arylated products are found in various fields of chemistry and represent essential entities for many applications. Therefore, the formation of this structural feature represents a central issue of contemporary organic synthesis. By the action of electricity the necessity of leaving groups, metal catalysts, stoichiometric oxidizers, or reducing agents can be omitted in part or even completely. The replacement of conventional reagents by sustainable electricity not only will be environmentally benign but also allows significant short cuts in electrochemical synthesis. In addition, this methodology can be considered as inherently safe. The current survey is organized in cathodic and anodic conversions as well as by the number of leaving groups being involved. In some electroconversions the reagents used are regenerated at the electrode, whereas in other electrotransformations free radical sequences are exploited to afford a highly sustainable process. The electrochemical formation of the aryl–substrate bond ...

Electrochemical Arylation Reaction.

Nucleophilic substitution reactions by electron transfer

A series of conjugated zinc porphyrin oligomers, from the dimer through to the hexamer, form stable ladder complexes with linear bidentate ligands such as 1,4-diazabicyclo[2.2.2]octane (DABCO) and 4,4‘-bipyridyl (Bipy). The 1H NMR spectra of these ladders confirm their structures and show how they fray and dissociate in the presence of excess ligand. The thermodynamics of these equilibria were elucidated by spectrophotometric titration, using multivariate global factor analysis, in two different solvents (chloroform and toluene). Ladder formation and dissociation exhibit many indications of positive cooperativity, including all-or-nothing two-state assembly, sigmoidal isotherms, large Hill coefficients, and narcissistic self-sorting. Ladder formation increases the planarity and conjugation, resulting in a reduction in the gap between the highest occupied and lowest unoccupied molecular orbitals.

Cooperative Self-Assembly of Double-Strand Conjugated Porphyrin Ladders

Desulfonylation reactions: Recent developments

Oxidation of Carbanions with Lithium tert-Butyl Peroxide

Electrochemically catalyzed aromatic nucleophilic substitution. Phenoxide ion as nucleophile

Reduction-Promoted Sulfur-Oxygen Bond Cleavage in a Nickel Sulfenate as a Model for the Activation of [NiFe] Hydrogenase

Electrosynthesis of unsymmetrical biaryls using a SRN1 type reaction

Electron paramagnetic resonance and electrochemical study of the oxidation chemistry of mononuclear and binuclear chromium carbonyl thiolates

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