Synthesis of fluorinated acid-functionalized, electron-rich nickel porphyrins

• Mike Brockmann,
• Jonas Lobbel,
• Lara Unterriker and
• Rainer Herges

Beilstein J. Org. Chem. 2024, 20, 2954–2958, doi:10.3762/bjoc.20.248

• 4 (65%), 5 (50%), and 6 (40%) by chromatography was straightforward. However, the subsequent oxidation of the alcohol with the usual oxidizing agents (Jones reagent, KMnO4, etc.) was not successful. A radical oxidation with TEMPO, potassium bromide (KBr), sodium hypochlorite (NaOCl), and sodium

(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

• Nataliia V. Kirij,
• Andrey A. Filatov,
• Yurii L. Yagupolskii,
• Sheng Peng and
• Lee Sprague

Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40

• ]. A few decades later, several new publications in this direction appeared in the literature. In a Chemours’ patent, it has been shown that the oxidation of (E)-butene 1a with sodium hypochlorite in the presence of tetrabutylphosphonium bromide leads to the formation of a bistrifluoromethyl containing

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• contortus (Haecon-5 strain) larvae (L3s) were produced and stored using an established protocol [45] – approved by the animal ethics committee of the University of Melbourne (permit no. 1714374). For use in the assay, L3s were exsheathed and sterilized by incubation in 0.15% (v/v) sodium hypochlorite (NaClO

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• , 29.74, 29.53, 25.38, 22.82, 22.25, 21.63, 15.59; HRMS (m/z): [M + Na]+ calcd, 383.1829; found, 383.1825. Chemical oxidation of 9,11-dihydroxysteroids The general procedure of Kirihara et al. [31] was followed. Sodium hypochlorite pentahydrate (3 equiv) was added to a stirred solution of diol (1 equiv

Metal-free mechanochemical oxidations in Ertalyte^® jars

• Andrea Porcheddu,
• Francesco Delogu,
• Lidia De Luca,
• Claudia Fattuoni and
• Evelina Colacino

Beilstein J. Org. Chem. 2019, 15, 1786–1794, doi:10.3762/bjoc.15.172

• l’Ecole Normale, 34296 Montpellier, Cedex 5, France 10.3762/bjoc.15.172 Abstract Aimed at eliminating or at least significantly reducing the use of solvents, sodium hypochlorite pentahydrate crystals (NaOCl·5H2O) in the presence of a catalytic amount of a nitrosyl radical (TEMPO or AZADO) have been

• . In particular, in this study, we used sodium hypochlorite pentahydrate (NaOCl·5H2O) in the presence of a catalytic amount of a nitrosyl radical (TEMPO or AZADO) to induce mechanochemical oxidation reactions on suitably selected primary and secondary alcohols. Performed in a high-energy ball mill and

• process [55]. Also, Oxone® and NH2CONH2·H2O2 appeared to fail in the oxidation of 3-phenyl-1-propanol (1a) to the corresponding aldehyde. Subsequently, we turned our attention to sodium hypochlorite (NaOCl), an inexpensive and widely used oxidizing reagent also applied as a disinfectant and household

Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae

• Arin Gucchait,
• Angana Ghosh and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2019, 15, 431–436, doi:10.3762/bjoc.15.37

• the presence of TMSOTf [35] furnished target pentasaccharide derivative 20 in 70% yield (Scheme 4). Removal of the benzoyl group from compound 20 using sodium methoxide [24] followed by TEMPO-mediated oxidation [39] of the hydroxy group to a carboxylic group using sodium hypochlorite under biphasic

A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines

• Katherine E. Jolley,
• Michael R. Chapman and
• A. John Blacker

Beilstein J. Org. Chem. 2018, 14, 2220–2228, doi:10.3762/bjoc.14.196

• , though both exhibit poor atom economy [17][18][19][20][21]. Sodium hypochlorite (NaOCl) solutions are less widely used, yet readily available, economic and provide an atom efficient reagent for N-chloramine formation [22][23][24]. A continuous-flow process for the oxidation of alcohols using NaOCl as a

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

• Santanu Hati,
• Ulrike Holzgrabe and
• Subhabrata Sen

Beilstein J. Org. Chem. 2017, 13, 1670–1692, doi:10.3762/bjoc.13.162

• to generate the desired substituted dihydroquinazolines 35 in moderate to excellent yields (Scheme 9) [44]. In another example commercially available sodium hypochlorite (NaOCl) was used as an oxidant, under mild conditions in a highly efficient oxidative dehydrogenative coupling of o

Experimental and theoretical investigations into the stability of cyclic aminals

• Edgar Sawatzky,
• Antonios Drakopoulos,
• Martin Rölz,
• Christoph Sotriffer,
• Bernd Engels and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221

• ] (Scheme 2). Furthermore, copper-catalysed reactions or oxidation with sodium hypochlorite were also described to yield the aromatic quinazoline core [26][29][30] (Scheme 2). Besides all the oxidation reactions described, also reductive conditions applying NaBH4 onto the tetrahydroquinazoline-based aminal

Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts

• Laura A. Bryant,
• Rossana Fanelli and
• Alexander J. A. Cobb

Beilstein J. Org. Chem. 2016, 12, 429–443, doi:10.3762/bjoc.12.46

• , cupreine and cupreidine PTCs HCPN-65 and HCPD-67 were used in the epoxidation of the cis-α,β-unsaturated ketone 63 with sodium hypochlorite [53][54]. Interestingly, the use of these pseudoenantiomers did not lead to similar magnitudes of stereoselection in the opposite enantiomers of epoxide 64 that they

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• substituents and a free flowing solution. Subsequent addition of FCA− (Fe(0)) results in preferential complexation between β-CD and FCA− such that the PAAddn hydrogel reforms. This situation is reversed upon oxidation of FCA− with sodium hypochlorite to FCA (Fe(I)) which is complexed much less strongly by β-CD

Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors

• A. John Blacker and
• Katherine E. Jolley

Beilstein J. Org. Chem. 2015, 11, 2408–2417, doi:10.3762/bjoc.11.262

• solutions of N,N-dialkyl-N-chloramines is described using either a bespoke meso-scale tubular reactor with static mixers or a continuous stirred tank reactor. Both reactors promote the efficient mixing of a biphasic solution of N,N-dialkylamine in organic solvent, and aqueous sodium hypochlorite to achieve

• solutions of N,N-dialkyl-N-chloramines produced continuously will enable their use in tandem flow reactions with a range of nucleophilic substrates. Keywords: amine; biphasic; chloramine; chlorination; continuous flow chemistry; CSTR; static mixer; sodium hypochlorite; tube reactor; Introduction N

• alkenes to make amines, aldehydes to make amides, and base to make imines is ongoing. Experimental All reagents were used as received from suppliers without purification. Sodium hypochlorite solution 10–15% available chlorine was purchased from Sigma-Aldrich. The accurate NaOCl concentration was

The preparation of new functionalized [2.2]paracyclophane derivatives with N-containing functional groups

• Henning Hopf,
• Swaminathan Vijay Narayanan and
• Peter G. Jones

Beilstein J. Org. Chem. 2015, 11, 437–445, doi:10.3762/bjoc.11.50

• had converted its pseudo-geminal isomer 7 by sodium hypochlorite oxidation into the corresponding azo compound [20] we also attempted this transformation for 8. The intended, chiral azo compound 17 was, however, not produced. Presumably the two amino functions are too far apart for intramolecular

The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates

• Katharina Gallas,
• Gerit Pototschnig,
• Florian Adanitsch,
• Arnold E. Stütz and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2012, 8, 1619–1629, doi:10.3762/bjoc.8.185

• . HCN was transferred in a nitrogen stream through a drying column (CaCl2) and collected in a cooling trap at −12 °C. Waste solutions containing cyanides were treated with aqueous sodium hypochlorite (10%). General procedure for preparation of aldoheptoses [32]: The respective aldose was dissolved in

Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

• Sarah L. Harding,
• Sebastian M. Marcuccio and
• G. Paul Savage

Beilstein J. Org. Chem. 2012, 8, 606–612, doi:10.3762/bjoc.8.67

• chemical shift of the C(H)=N proton [34]. Attempted methods for the chlorination of aryl aldoximes to aryl hydroximoyl chloride include the use of N-chlorosuccinimide [35], chloramine-T [36], biphasic sodium hypochlorite [37][38], and tert-butyl hypochlorite [39]. These methods led to either no reaction or

Mitomycins syntheses: a recent update

• Jean-Christophe Andrez

Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33

• disconnection 5.1. Kozikowski. Nitrile oxide cycloaddition, INOC The Kozikowski group used an intramolecular nitrile oxide cycloaddition (INOC) to form the eight membered ring of a benzazocine system [101]. The hydroxylamine 120 was treated with sodium hypochlorite to generate in situ a nitrile oxide which

• oppose this orientation (Scheme 36). This methodology was used later on by the Fukuyama group to achieve the synthesis of mitomycin analogs [102]. Treating hydroxylamine 127 with sodium hypochlorite effected the cycloaddition, but the wrong regioisomer 128 was obtained (Scheme 37). Steric repulsions

A biphasic oxidation of alcohols to aldehydes and ketones using a simplified packed- bed microreactor

• Andrew Bogdan and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2009, 5, No. 17, doi:10.3762/bjoc.5.17

• output of a reaction and is of higher throughput than other reported packed-bed microreactors. Experimental General Solvents were purified by standard procedures. All other reagents were used as received, unless otherwise noted. Sodium hypochlorite solution (reagent grade, available chlorine 10–15%) was