Recent advances in the electrochemical synthesis of organophosphorus compounds

• Babak Kaboudin,
• Milad Behroozi,
• Sepideh Sadighi and
• Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

• phosphite in an undivided cell. The C–P product was selectively produced using n-Bu4NClO4 as electrolyte and carbon and platinum electrodes as the anode and cathode at a constant current for 4 h. Using n-Bu4NI instead of KI resulted in a similar outcome, but KBr was less effective (Table 4). The desired C2

Recent advances in electrochemical copper catalysis for modern organic synthesis

• Yemin Kim and
• Won Jun Jang

Beilstein J. Org. Chem. 2025, 21, 155–178, doi:10.3762/bjoc.21.9

• employing electricity as an oxidant (Figure 11) [60]. Mechanistic studies have indicated that n-Bu4NI acts as a redox mediator at the anode, and the electron transfer between the copper complex and the iodine radical is the rate-determining step. The author proposed a catalytic cycle, as illustrated in

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• . In a recent study, Zheng et al. introduced a highly effective photocatalytic approach for the decarboxylative conversion of redox-active esters 10, leading to the efficient synthesis of olefins 11. This process was conducted in the presence of n-Bu4NI, as illustrated in Scheme 6 [12]. The utilization

• . An EDA complex was formed through non-covalent interaction between the redox ester 10 and n-Bu4NI (Scheme 7). Subsequently, upon the photoexcitation, radical pairs I were generated via a SET process, accompanied by the liberation of CO2 and the phthalimide anion. The recombination of the alkyl

• NaI/PPh3 catalysis. Decarboxylative alkenylation mediated by NaI/PPh3 catalysis. NaI-mediated photoinduced α-alkenylation of Katritzky salts 7. n-Bu4NI-mediated photoinduced decarboxylative olefination. Proposed mechanism of the n-Bu4NI-mediated photoinduced decarboxylative olefination

Functionalization of N-arylglycine esters: electrocatalytic access to C–C bonds mediated by n-Bu₄NI

• Mi-Hai Luo,
• Yang-Ye Jiang,
• Kun Xu,
• Yong-Guo Liu,
• Bao-Guo Sun and
• Cheng-Chu Zeng

Beilstein J. Org. Chem. 2018, 14, 499–505, doi:10.3762/bjoc.14.35

• Business University, Beijing 100048, China 10.3762/bjoc.14.35 Abstract An efficient electrocatalytic functionalization of N-arylglycine esters is reported. The protocol proceeds in an undivided cell under constant current conditions employing the simple, cheap and readily available n-Bu4NI as the mediator

• . In addition, it is demonstrated that the mediated process is superior to the direct electrochemical functionalization. Keywords: C–C formation; electrochemical oxidative functionalization; n-Bu4NI; redox catalyst; Introduction The oxidative cross dehydrogenative coupling (CDC) of two C–H bonds has

• electrochemical C–H bond functionalization, leading to the formation of new C–C, C–N, C–O and C–S bonds [28][29][30][31]. Herein, we report the electrochemical α-C–H functionalization of N-arylglycine esters with C–H nucleophiles using n-Bu4NI as redox catalyst (Scheme 1). The chemistry was performed in an

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na₂S₂O₈

• Teppei Sasaki,
• Katsuhiko Moriyama and
• Hideo Togo

Beilstein J. Org. Chem. 2018, 14, 345–353, doi:10.3762/bjoc.14.22

• [27], with R-CH=O/(n-Bu)4NBr (TBAB, cat.)/K2S2O8 at 90 °C [28], with ArSO2H/Eosin Y(cat.)/tert-butyl hydrogen peroxide (TBHP) at rt [29], and with ArSO2NHNH2/n-Bu4NI(cat.)/TBHP at 80 °C [30]. In addition, the formation of coumarins via the bromine-radical-mediated reaction of aryl 2-alkynoates with

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF₃SO₂Cl

• Hélène Chachignon,
• Hélène Guyon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2800–2818, doi:10.3762/bjoc.13.273

• this proposed mechanism, bis(trifluoromethyl)disulfide (CF3SSCF3) was generated but its possible role in the trifluoromethylsulfenylation was not evoked. A slight tuning of the reaction conditions, including notably a replacement of NaI by n-Bu4NI, as well as the increase of reagents quantities

• )arenes and thiols. PPh3/NaI-mediated trifluoromethylsulfenylation of indole derivatives. PPh3/n-Bu4NI mediated trifluoromethylsulfenylation of thiophenol derivatives. PPh3/Et3N mediated trifluoromethylsulfinylation of benzylamine. PCy3-mediated trifluoromethylsulfinylation of azaarenes, amines and

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

p-tert-Butylthiacalix[4]arenes functionalized by N-(4’-nitrophenyl)acetamide and N,N-diethylacetamide fragments: synthesis and binding of anionic guests

• Alena A. Vavilova and
• Ivan I. Stoikov

Beilstein J. Org. Chem. 2017, 13, 1940–1949, doi:10.3762/bjoc.13.188

• macrocycles studied with n-Bu4NH2PO4 and n-Bu4NF. Besides, changes were observed when the macrocycle 6 interacted with n-Bu4NCH3CO2 and in the case of the compound 3, when n-Bu4NCl, n-Bu4NBr, n-Bu4NI, n-Bu4NCH3CO2, and n-Bu4NNO3 were added. In the absorption spectra of the thiacalix[4]arene 5 with n-Bu4NX

Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives

• Yan Li,
• Xue Zhou,
• Guangfan Zheng and
• Qian Zhang

Beilstein J. Org. Chem. 2015, 11, 2721–2726, doi:10.3762/bjoc.11.293

• aminooxygenation reaction of alkenes with phthalimide and (diacetoxyiodo)benzene through cis-aminopalladation and SN2 C–O bond formation [34]. In 2013, Zhu and co-workers described an n-Bu4NI-catalyzed aminooxygenation of inactive alkenes with benzotriazole and water which underwent a nitrogen-centred radical

Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands

• Silvia Bernardi,
• Paola Fezzardi,
• Gabriele Rispoli,
• Stefania E. Sestito,
• Francesco Peri,
• Francesco Sansone and
• Alessandro Casnati

Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175

• ]arenes 3. Reaction conditions: (i) NaN3, n-Bu4NI, DMF, 90 °C, 24 h, 60%; (ii) CuSO4·5H2O, Na-ascorbate, DMF/H2O, μW (150 W), 80 °C, 40 min, 46%; (iii) CH3ONa, CH3OH, rt, 2 h – IR120/H+, rt, 30 min, 73%. Synthesis of the 1,3-alternate lactosylcalix[4]arenes 4. Reaction conditions: (i) EDC, CH2Cl2/py (7:3

Structure elucidation of female-specific volatiles released by the parasitoid wasp Trichogramma turkestanica (Hymenoptera: Trichogrammatidae)

• Armin Tröger,
• Teris A. van Beek,
• Martinus E. Huigens,
• Isabel M. M. S. Silva,
• Maarten A. Posthumus and
• Wittko Francke

Beilstein J. Org. Chem. 2014, 10, 767–773, doi:10.3762/bjoc.10.72

• h; 2) BnBr (1 equiv), n-Bu4NI, 0 °C to rt, 16 h; i: PCC, MS 4 Å, DCM, −20°C, 90 min; j: [(E)-1-methylbut-2-en-1-yl]triphenylphosphonium bromide, n-BuLi, THF, −40 °C, 14 h; k: H2, 20 bar, 10% Pd/C, pentane, rt, 18 h. 70 eV EIMS of synthetic tetramethyltrideca-2,4-dienes 8, 14 and 15. These spectra