Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

• Mana Kitano,
• Tsuyoshi Saitoh,
• Shigeru Nishiyama,
• Yasuaki Einaga and
• Takashi Yamamoto

Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119

• 10.3762/bjoc.18.119 Abstract A straightforward electro-conversion of cumene into acetophenone has been reported using boron-doped diamond (BDD) electrodes. This particular conversion is driven by the addition reaction of a cathodically generated hydroperoxide anion to an anodically generated cumyl cation

• /or cathode. Boron-doped diamond (BDD) is a relatively new electrode material [15][16] and shows a wide potential window, which can be applied to the transformation of compounds with high redox potentials. Therefore, BDD electrodes would enable a straightforward oxidation reaction of aromatic alkyls

• straightforward electro-conversion of cumene into acetophenone using boron-doped diamond (BDD) electrodes. The BDD’s wide potential window enabled the direct anodic oxidation of cumene to afford a key reaction intermediate, which cannot be realized by other electrodes such as graphite and Ni. Electrosynthesis is

Direct electrochemical generation of organic carbonates by dehydrogenative coupling

• Tile Gieshoff,
• Vinh Trieu,
• Jan Heijl and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2018, 14, 1578–1582, doi:10.3762/bjoc.14.135

• reactive chemicals. We present the first direct electrochemical generation of mesityl methyl carbonate by C–H activation. Although this reaction pathway is still challenging concerning scope and efficiency, it outlines a new strategy for carbonate generation. Keywords: anode; boron-doped diamond

• method for the generation of organic carbonates using inexpensive starting materials without the necessity of catalysts. Generally, alcohols serve as starting materials for the DPC and DMC synthesis. However, efficiency increases if non-functionalized aromatic compounds serve as feedstock. Boron-doped

• diamond (BDD) as electrode material has the capability to convert simple aromatic systems by direct C–H activation [21][22][23][24][25][26][27]. In contrast, other typical anode materials such as graphite, glassy carbon, or platinum tend to lead to electrode fouling when applying high positive potentials

Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

• Taiki Kojima,
• Rika Obata,
• Tsuyoshi Saito,
• Yasuaki Einaga and
• Shigeru Nishiyama

Beilstein J. Org. Chem. 2015, 11, 200–203, doi:10.3762/bjoc.11.21

• methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate. Two new neolignan

• -type products were synthesized from the hydrodimer. Keywords: boron-doped diamond (BDD) electrode; cathodic reduction; electrochemistry; electrosynthesis; neolignan; Introduction Numerous lignans and neolignans were found as secondary plant metabolites, and many of them are known to exhibit

• investigations. Several synthetic approaches, including electrochemical oxidative coupling reactions mimicking biosynthetic pathways, were reported to construct the backbones of these molecules [5]. Recently, boron-doped diamond (BDD) electrodes have attracted a great deal of attention for their wide potential

Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids

• Roman Matthessen,
• Jan Fransaer,
• Koen Binnemans and
• Dirk E. De Vos

Beilstein J. Org. Chem. 2014, 10, 2484–2500, doi:10.3762/bjoc.10.260

• prepared using cyanides. In the proposed setup for the electrocatalytic preparation of MHA, a boron-doped diamond coated permeable cathode and Pt coated permeable anode rest directly on the cation exchange membrane to decrease ohmic resistance by the membrane, minimizing the required voltage. Hydrogen