Parallel Electrosynthesis of α-Alkoxycarbamates, α-Alkoxyamides, and α-Alkoxysulfonamides Using the Spatially Addressable Electrolysis Platform (SAEP)

Abstract

The spatially addressable electrolysis platform (SAEP) has been designed and constructed. It is demonstrated that the advantages of electrochemistry can be readily adapted to combinatorial chemistry and parallel synthesis formats. Parallel electrosynthesis of alpha-alkoxycarbamates, alpha-alkoxyamides, and alpha-alkoxysulfonamides via anodic oxidation of carbamates, amides, and sulfonamides, respectively, highlights the main features of the SAEP.

A Century of Organic Electrochemistry

“…Substitution in the aromatic ring requires the presence of acetate ion. 120 When acetonitrile containing some trifluoracetic anhydride is the solvent, the carbocation formed by oxidation may attack the solvent in a Ritter-type reaction; methylsubstituted benzenes are good substrates for such an acetamidation. 121 Even n-alkanes may be oxidized in MeCN/R 4 NBF 4 with acetamidation at a secondary carbon.…”

Regioselectivity of Electrochemical C-H Functionalization Via Iminium Ion

“…That this is as explained is corroborated by the fact that higher yield and selectivity to the ␣-alkoxylated product is [36] obtained when the current density is increased, thus entailing higher electric fields at the interface and tighter orientation of the molecules. On the other hand, Libendi et al [20] tried a selective activation of the most substituted site by changing the Boc group by a CN protecting group.…”

Development of a Novel Environmentally Friendly Electrolytic System by Using Recyclable Solid‐Supported Bases for In Situ Generation of a Supporting Electrolyte from Methanol as a Solvent: Application for Anodic Methoxylation of Organic Compounds

“…After the electrolysis, the electrolytic solution was passed through a glass filter (pore size: 10-16 mm) to remove the solid-supported bases. The filtrate was evaporated to provide a pure methoxylated product, which was identified by authentic samples (7 b , 8 b, 10 b, 12 b, 13 b, 13 c, 14 b, and 15 b) and literatures (4, [13] 5b, [18] 6b, [18] 9b, [19] and 11 b [20] ) using 1 H, 19 F NMR and Mass spectroscopy. However, when the yield of a methoxylated product was low, the residue was purified by Shimadzu LC-6AD liquid chromatography eluting with CH 3 CN to give a pure methoxylated product.…”