Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• heteroatoms (nitrogen, sulfur, selenium, tellurium, etc.) as well as redox-active functional groups allows one to vary significantly the biological activity of such compounds. Heterocyclic molecular blocks are widely used in medicinal chemistry [12]. Thiazole, oxadiazole, triazole, imidazole, and other

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

• Akiya Ogawa and
• Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

• (ArTe-C•(=NR’)) could not be observed. However, the tellurium group of RTeAr can successfully trap the imidoyl radicals to yield the corresponding isocyanide-inserted organotellurium compounds (Scheme 6) [34][35][36]. Radical addition of group 15 compounds to isocyanides Tetrakis(trimethylsilyl

• thioselenation and catalytic dithiolation of isocyanides. Synthesis of carbacephem framework. Sequential addition of (PhSe)2 to ethyl propiolate and isocyanide. Isocyanide insertion reaction into carbon-tellurium bonds. Radical addition to isocyanides with disubstituted phosphines. Radical addition to phenyl

A comparison of structure, bonding and non-covalent interactions of aryl halide and diarylhalonium halogen-bond donors

• Nicole Javaly,
• Theresa M. McCormick and
• David R. Stuart

Beilstein J. Org. Chem. 2024, 20, 1428–1435, doi:10.3762/bjoc.20.125

• -qzvpp for iodine and tellurium and in the gas phase. In our present work using M06-2x/6-311+G(d) with def2-txvpp for iodine and astatine, we observed excellent agreement in the correlation between orbitals used on the halonium center and the C–X–C bond angle, i.e., molecular geometry, from our prior

Phenotellurazine redox catalysts: elements of design for radical cross-dehydrogenative coupling reactions

• Alina Paffen,
• Christopher Cremer and
• Frederic W. Patureau

Beilstein J. Org. Chem. 2024, 20, 1292–1297, doi:10.3762/bjoc.20.112

• substitution patterns on the redox catalytic activity. Keywords: cross-dehydrogenative coupling; O2 activation; phenotellurazine; redox catalysis; Te catalysis; Introduction Tellurium catalysis has become increasingly important in recent years. This is due to its unique chalcogen bonding ability, thus

• , which exploit the redox flexibility of tellurium, especially in the context of phenotellurazine scaffolds. Notably, we showed that phenotellurazine PTeZ1 could significantly catalyze the cross-dehydrogenative phenothiazination of phenols bearing challenging electron-withdrawing substituents under a

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• thiepines were progressively isolated as a result of very diverse synthetic strategies [46][47][48][49], which were further applied to the preparation of stable selenepines and tellurepines [50][51][52][53]. Extrusion reactions from sulfur-, selenium- and tellurium-containing compounds have long been

• design of pentacene’s soluble precursor, as reported by Müllen and Herwig [14], is depicted in the top left. Valence isomerization of chalcogen heteropines and subsequent cheletropic extrusion in the case of sulfur, selenium and tellurium derivatives. Early example of phenanthrene synthesis via a

Synthesis and reactivity of azole-based iodazinium salts

• Thomas J. Kuczmera,
• Annalena Dietz,
• Andreas Boelke and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 317–324, doi:10.3762/bjoc.19.27

• phenotellurazine 7c were isolated in lower yields of 16% and 6%, likely due to undesired oxidations of selenium and tellurium [38]. Substitutions with nitrogen nucleophiles were performed, giving the N-phenylphenazine 8 in 26% yield [39][40] and the N-tosyl derivative 9 in 18% yield [41]. Anion exchange reactions

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

• Ranadeep Talukdar

Beilstein J. Org. Chem. 2021, 17, 2102–2122, doi:10.3762/bjoc.17.137

• , nitrogen, oxygen, silicon, phosphorus, sulfur, selenium, and tellurium. This review will skip the reports on the corresponding carbon-centered analogs. Boranes First discovered in 1894 [34], 2,2’-bisarylborinates are used for treating prostate cancers utilizing their property of inhibiting the transient

• 149 of the N-sulfonyl-protected indole 1o with metallic Te in four steps including desulfonylation (Scheme 19) [99]. The treatment with base followed by the addition of elemental tellurium to N-protected indole 1o generates lithium telluride 150. Telluride 150 is then oxidized to ditelluride 151 by

Simulating the enzymes of ganglioside biosynthesis with Glycologue

• Andrew G. McDonald and
• Gavin P. Davey

Beilstein J. Org. Chem. 2021, 17, 739–748, doi:10.3762/bjoc.17.64

• ], Tellurium [39], or other modelling software supporting this format. Glycan structures can be imported or exported as GlycoCT [40], and exported as Linear Code [41] or IUPAC condensed linear formats. Sets of structures can be downloaded as CSV or GlycoCT. A key function of Glycologue is the ability to

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

•  43, the hexalithiation of 152 was accomplished using butyllithium in the presence of TMEDA which on further treatment with tellurium powder afforded the desired product 162 in 30% yield with 60% starting material recovery. Along similar lines, they also assembled compound 163 in 25% yield as

• displayed in Scheme 43. Furthermore, when they subjected the tritellurasumanenes 162 and 163 with Br2 in CH2Cl2, they obtained the tris(Te,Te-dibromo)tritellurasumanenes 164 and 165 as covalent adducts in quantitative yield (Scheme 43). 3.4 Preparation of sulfur, selenium and tellurium-doped sumanenes The

• transformed to the ortho-quinones in the presence of FeCl3. From the experimentations, they noticed that heteroatoms also play a significant role in this reaction for instance with sulfur and selenium-doped systems, ortho-quinones 166 and 167 were obtained (Scheme 44). In sharp contrast, the tellurium-doped

Regio- and stereoselective synthesis of new ensembles of diversely functionalized 1,3-thiaselenol-2-ylmethyl selenides by a double rearrangement reaction

• Svetlana V. Amosova,
• Andrey A. Filippov,
• Nataliya A. Makhaeva,
• Alexander I. Albanov and
• Vladimir A. Potapov

Beilstein J. Org. Chem. 2020, 16, 515–523, doi:10.3762/bjoc.16.47

• & Tellurium at the beginning of the 3rd millennium" [40]. Our short preliminary publication reported the formation of 1,3-thiaselenol-2-ylmethyl selenocyanate (4) in the reaction thiaselenole 1 with selenocyanate [47]. Results and Discussion In this work the nucleophilic substitution reaction of thiaselenole

A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

• Thines Kanagasundaram,
• Antje Timmermann,
• Carsten S. Kramer and
• Klaus Kopka

Beilstein J. Org. Chem. 2019, 15, 2569–2576, doi:10.3762/bjoc.15.250

• be an effective catalyst for the synthesis of rhodamine and rosamine dyes as well as for their selenium or tellurium analogous [29], the usage of that Pd(0) catalyst showed yields comparable with those obtained with PdCl2(PPh3)2 (Table 1, entry 4). The exchange of sodium carbonate with cesium

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• (iodine, bromine) and chalcogens (selenium and tellurium) [18]. While there are several strategies for the synthesis of triazoles, the Cu(II)-catalyzed azide–alkyne cycloaddition reaction (CuAAC click reaction) is considered as one of the most efficient, simple and mild approaches towards the preparation

Synthesis of benzo[d]imidazo[2,1-b]benzoselenoazoles: Cs₂CO₃-mediated cyclization of 1-(2-bromoaryl)benzimidazoles with selenium

• Mio Matsumura,
• Yuki Kitamura,
• Arisa Yamauchi,
• Yoshitaka Kanazawa,
• Yuki Murata,
• Tadashi Hyodo,
• Kentaro Yamaguchi and
• Shuji Yasuike

Beilstein J. Org. Chem. 2019, 15, 2029–2035, doi:10.3762/bjoc.15.199

• reaction of 1a with sulfur or tellurium powder did not proceed, and the starting material 1a was recovered (Table 1, entries 17 and 18). The best result was obtained when 1a and Se powder were treated with Cs2CO3 in DMF under an argon atmosphere at 150 °C. The benzimidazo[2,1-b]benzoselenoazole product 2a

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

• András György Németh,
• György Miklós Keserű and
• Péter Ábrányi-Balogh

Beilstein J. Org. Chem. 2019, 15, 1523–1533, doi:10.3762/bjoc.15.155

• isocyanides and sulfur [76] can be enhanced using various catalysts such as selenium, molybdenum, copper, rhodium [77][78][79][80][81][82] or tellurium [83] providing the isothiocyanates in excellent yields. These approaches on the other hand suffer from the use of heavy metals, toxic chalcogens and/or long

Cobalt–metalloid alloys for electrochemical oxidation of 5-hydroxymethylfurfural as an alternative anode reaction in lieu of oxygen evolution during water splitting

• Jonas Weidner,
• Stefan Barwe,
• Kirill Sliozberg,
• Stefan Piontek,
• Justus Masa,
• Ulf-Peter Apfel and
• Wolfgang Schuhmann

Beilstein J. Org. Chem. 2018, 14, 1436–1445, doi:10.3762/bjoc.14.121

• Te), could likewise lead to an enhanced electrocatalysis for reactions other than the OER and the HER. To this end, alloys of cobalt with boron, silicon, phosphorus, arsenic and tellurium were screened for their electrocatalytic activity for HMF oxidation. A detailed synthetic procedure to afford

• heating step to 1100 °C with an isothermal step for 20 h. The mixture was subsequently cooled to room temperature to give CoAs. Cobalt telluride, CoTe. Cobalt telluride was synthesized from the elements Co (0.948 g) and tellurium (2.052 g). The ampule was heated to 800 °C followed by an isothermal step

Catalytic Wittig and aza-Wittig reactions

• Zhiqi Lao and
• Patrick H. Toy

Beilstein J. Org. Chem. 2016, 12, 2577–2587, doi:10.3762/bjoc.12.253

• section summarizes how arsenic and tellurium-based catalytic Wittig-type reaction systems were developed first due to the relatively easy reduction of the oxides involved. This is followed by a presentation of the current state of the art regarding phosphine-catalyzed Wittig reactions. The second section

• that Huang and co-workers reported their catalytic reactions using 3 (Scheme 2), they also disclosed that Bu2Te (15) could function similarly as a catalyst in such Wittig-type reactions due to the relatively weak tellurium–oxygen bond of dialkyl telluroxides, such as Bu2Te=O (16) (Scheme 4) [13

• loading level (0.2 equivalents) and with a similar set of aldehyde 6 substrates. Tang’s research group also followed up this tellurium-based research many years later and published several papers describing the use of polymer-supported tellurides, such as 18, as catalysts (Scheme 5) [14][15][16]. The

New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand

• Agnieszka Hryniewicka,
• Szymon Suchodolski,
• Agnieszka Wojtkielewicz,
• Jacek W. Morzycki and
• Stanisław Witkowski

Beilstein J. Org. Chem. 2015, 11, 2795–2804, doi:10.3762/bjoc.11.300

• of the nitro group in 11 was slightly troublesome, probably due to steric hindrance. The tellurium-rongalit system was found to be the most efficient [30], and 6-chromanylamine 12 was obtained in 50% yield. Imidazolinium salt 14 was prepared according to the classical protocol. Chromanylamine 12 was

• ) tellurium powder (154 mg, 0.2 equiv, 1.2 mmol) was added. Then the solution of 6-nitro-2,2,5,7,8-pentamethylchromane (11, 1.5 g, 6 mmol) in dioxane (20 mL) was added to the reaction mixture. The reaction was carried out at 50 °C for 8 h. The reaction mixture was filtered through a pad of Celite and the

Attempts to prepare an all-carbon indigoid system

• Şeref Yildizhan,
• Henning Hopf and
• Peter G. Jones

Beilstein J. Org. Chem. 2015, 11, 363–372, doi:10.3762/bjoc.11.42

• ): representing the basic cross-conjugated π-electron system of the indigoid compounds [7][8][9]. Whereas the replacement of Y in 2 (X = O) by sulfur and selenium [10][11] or even tellurium [12][13] has been known for some time, derivatives of “phosphaindigo” (Y = various substituted phosphorus derivatives) have

The renaissance of organic radical chemistry – deja vu all over again

• Corey R. J. Stephenson,
• Armido Studer and
• Dennis P. Curran

Beilstein J. Org. Chem. 2013, 9, 2778–2780, doi:10.3762/bjoc.9.312

• ][14][15][16], e) radical trifluoromethylation [17] and radical fluorination [18][19][20], f) natural product synthesis [21], g) new main group radical chemistry involving elements like boron [22], phosphorous [23] and selenium [24], tellurium [25], among others, h) synthesis or functionalization of

Organotellurium-mediated living radical polymerization under photoirradiation by a low-intensity light-emitting diode

• Yasuyuki Nakamura and
• Shigeru Yamago

Beilstein J. Org. Chem. 2013, 9, 1607–1612, doi:10.3762/bjoc.9.183

• -emitting diode; living radical polymerization; organotellurium compound; photopolymerization; tellurium; visible light; Introduction Living radical polymerization (LRP) is one of the most powerful methods for the synthesis of structurally well-defined polymers because of its robustness and high

• the generation of tellurium radicals, which activate the organotellurium dormant species [30][39]. Therefore, the development of new photochemical conditions which employ a weak-intensity, readily available light source is necessary for expanding the utility of photo-TERP. We focused on a light

• and 87500, with narrow MWDs (Mw/Mn = 1.18 and 1.33, respectively) were successfully synthesized by using a 10% transmittance ND filter (Table 2, runs 6 and 7). When the ditelluride is absent, polymerization is initiated by the direct photolysis of the carbon–tellurium bond of the organotellurium

Homolytic substitution at phosphorus for C–P bond formation in organic synthesis

• Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 1269–1277, doi:10.3762/bjoc.9.143

• ). Notably, the sense of the regioselectivity of tellurophosphination by a PhTe–TePh/Ph2P–PPh2 system is opposite to those of the thio- and selenophosphination (Scheme 12). This reversal indicates that homolytic substitution at tellurium overwhelms that at phosphorus and that a diphenylphosphanyl radical is

Isotopically labeled sulfur compounds and synthetic selenium and tellurium analogues to study sulfur metabolism in marine bacteria

• Nelson L. Brock,
• Christian A. Citron,
• Claudia Zell,
• Martine Berger,
• Irene Wagner-Döbler,
• Jörn Petersen,
• Thorsten Brinkhoff,
• Meinhard Simon and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 942–950, doi:10.3762/bjoc.9.108

• -serine to L-cysteine. Elemental sulfur, hydrogen sulfide, or thiosulfate can be funneled via the lithotrophic sulfur oxidation (Sox) pathway to sulfate [18][19][20][21][22]. Analogous degradation steps for the selenium and tellurium derivatives of DMSP (dimethylseleniopropionate, DMSeP, and

• methaneselenol-derived volatiles, whereas the verification of tellurium-containing volatiles from DMTeP remained elusive [25]. Here we report the results of an in-depth investigation of sulfur metabolic pathways to volatile sulfur compounds in marine alphaproteobacteria by feeding of isotopically labeled sulfur

• compounds and synthetic selenium and tellurium analogues to wildtype and relevant mutant strains. A reinvestigation of DMTeP conversion by marine bacteria from the Roseobacter clade into methylated tellurium volatiles using a modified analytical technique is also presented. Results and Discussion Usage of

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

• Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

• in Scheme 35 [118]. It should be noted that the tellurium reagent, Me3SnTeCF3, is capable of introducing the TeCF3 group into activated heteroaromatics [119]. In the reaction shown (Scheme 36) the use of three equivalents resulted in the introduction of only two TeCF3 groups. The Sandmeyer reaction

Synthesis and properties of calix[4]arene telluropodant ethers as Ag⁺ selective sensors and Ag⁺, Hg²⁺ extractants

• Yang Lu,
• Yuanyuan Li,
• Song He,
• Yan Lu,
• Changying Liu,
• Xianshun Zeng and
• Langxing Chen

Beilstein J. Org. Chem. 2009, 5, No. 59, doi:10.3762/bjoc.5.59

• synthesized and their metal ion chemistry studied, producing a diverse range of structures and unprecedented electronic and redox response [38][39][40][41][42][43][44][45][46][47][48][49]. However, the use of the tellurium atoms as soft donors to design sensors and investigation of their ion selective

• -selective electrodes (ISEs) in our group and by our co-workers [50][51][52][53]. To continue our interest in the development of new ionophores, herein we describe the design and synthesis of three novel tweezer-like 25,27-dihydroxy-26,28-bis(phenyltelluroalkoxy)calix[4]arenes 6–8 composed of two tellurium

• shifts depending on the distance from O atoms or Te atoms, for example, those attached to the O atom appeared at 4.02–3.94 ppm and those close to the Te atom were found at 3.38–2.98 ppm. In addition, 13C NMR spectrum afforded some information about the influence of tellurium: the phenyl carbons attached

Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts

• Hélio A. Stefani,
• Rafael C. Guadagnin,
• Artur F. Keppler,
• Giancarlo V. Botteselle,
• João V. Comasseto and
• Carlos A. Suganuma

Beilstein J. Org. Chem. 2008, 4, No. 9, doi:10.1186/1860-5397-4-9

• -aryl [4], alkenyl-alkynyl [5], and alkenyl-aryl [6] cross-coupling reactions. Distinct from the most commonly explored hydrometallation reactions, the hydrotelluration of alkynes exclusively forms Z-vinylic tellurides [7]. Vinylic tellurides have the ability to undergo tellurium-metal exchange

• experiments using 3,5-dibromo-4-nitrosobenzenesulfonate (DBNBS), which is an appropriate spin trap for tellurium centered radicals [17]. Radical species were detected at the i and ii steps of the proposed route. In the first step (i, Scheme 1), the detected spectra contained a mixture of DBNBS radical adducts