Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

• Elena R. Lopat’eva,
• Igor B. Krylov,
• Dmitry A. Lapshin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

• organocatalyst forms hydrogen bonds with both H2O2 and cyclic ketones [66]. A chiral Brønsted acid was used as chirality source and activator of H2O2 for an asymmetric sulfoxidation reaction [67] (Scheme 4B). It is generally accepted that in asymmetric Brønsted acid catalysis the activation of both the

• ethanol). Brønsted acid catalysis by TsOH was also employed in a selective sulfoxidation employing PhI(OAc)2 as oxidant [69]. In this case another mode of catalysis was proposed, including the covalent bonding of the acid catalyst anion and the oxidant with the formation of PhI(OTs)OH as the catalytically

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• (StyA, StyB, and an NADH-regenerating enzyme) and two cofactors (NADH and FAD), with only an oxygenase component and its flavin prosthetic group (Scheme 46). In 2004, Liese reported the asymmetric sulfoxidation of thioanisole 145 with high productivity and excellent enantioselectivity using a

Fluorine-containing substituents: metabolism of the α,α-difluoroethyl thioether motif

• Andrea Rodil,
• Alexandra M. Z. Slawin,
• Nawaf Al-Maharik,
• Ren Tomita and
• David O’Hagan

Beilstein J. Org. Chem. 2019, 15, 1441–1447, doi:10.3762/bjoc.15.144

• ; sulfoxidation; Introduction Fluorine and fluorinated substituents are routinely used to modify the properties of lead compounds in medicinal chemistry and in bioactive discovery programmes [1][2]. To this end, aryl–F and aryl–CF3 are the most common modifications found in compounds registered in the patent

• oxidation of thioether 4. This sulfone was then incubated with C. elegans and it gave rise to demethylated phenol 8 as the sole metabolite, consistent with an active demethylation capacity of this fungus. Non-oxidised phenol 10 was also not observed in this study. Overall this suggests that sulfoxidation is

• mass spectrometry. Naphthalene 5 was fully converted. Again, initial sulfoxidation dominates, but the second oxidation of the sulfoxide to a sulfone appears to be a slower process, and is outcompeted by aryl hydroxylation reactions. The experiment was conducted three times under similar conditions, all

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

• the corresponding sulfides. Very recently, the same group reported of a controllable sulfenylation and sulfoxidation procedure starting from alkyl and aryl thiosulfates and diaryliodonium salts under visible-light catalysis with Eosin Y (Scheme 40) [75]. They observed that the reaction yields the

• , respectively. Radical cross-coupling with the thiosulfate salt forms a sulfide radical anion, which is oxidized to the respective sulfide adduct by regeneration Eosin Y. This sulfide-forming step counts also for the sulfoxidation reaction. However, selective oxidation of the sulfide to the respective sulfoxide

Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones

• Flavia Pop and
• Narcis Avarvari

Beilstein J. Org. Chem. 2015, 11, 1105–1111, doi:10.3762/bjoc.11.124

• , characterization and solid-state structures of the (S,S) and (R,R) enantiomers of DM-BEDT-TTF monosulfones 1 (Scheme 1). Results and Discussion In our previous studies dealing with the sulfoxidation of the BEDT-TTF donor we could selectively obtain the inner BEDT-TTF sulfoxide (Scheme 1) by using chiral sulfonyl

• that the oxidation of the outer sulfur atoms into sulfoxide or sulfone should only moderately influence the oxidation potential and thus provide more stable radical cation species. In order to access chiral precursors with controlled stereochemistry we decided to investigate the sulfoxidation of the DM

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

• Sebastian Reinelt,
• Daniel Steinke and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

• sulfide) containing copolymers is based on the oxidation of thioethers to more hydrophilic sulfoxides or sulfones [11][12]. The specific sulfoxidation of a polymer bound end-group, which is in the focus of our present work, has not yet been investigated. Polymeric materials exhibiting sensitivity to