Electrochemical allylations in a deep eutectic solvent

• Sophia Taylor and
• Scott T. Handy

Beilstein J. Org. Chem. 2024, 20, 2217–2224, doi:10.3762/bjoc.20.189

• 1:3 molar ratio of tetrabutylammonium bromide and ethylene glycol (TBAB/EG) [28]. Using the reaction of p-anisaldehyde with allyl bromide as a test case, reactions were performed using three sets of different sacrificial electrodes as well as non-sacrificial graphite. As can be seen in Table 1, tin

• starting material were recovered via extraction with methoxycyclopentane and the CC/EG used in another cycle. Through two recyclings, the reactions were similar in efficiency, although the DES became increasingly viscous as the tin byproducts built up and it became impractical to recycle the DES further

• flash column chromatography. In between reactions, the tin electrodes were rinsed with DI water and acetone, then polished using diamond polish. This helped prevent buildup on the electrode surfaces. General C/C procedure with TBAB/EG To a 10 mL ElectraSyn 2.0 vial containing a magnetic stir bar were

Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

• Andrey R. Galeev,
• Maksim V. Dmitriev,
• Alexander S. Novikov and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2024, 20, 2208–2216, doi:10.3762/bjoc.20.188

• reaction was expected, Figure 2) with morpholine under previously found conditions (Scheme 2). To our delight, the meta-1,2,4-oxadiazole aniline 3ab, formed by the sequence of aldol-type reactions, was isolated in 80% yield and its structure was confirmed by NMR and single crystal X-ray analysis (CCDC

• desired meta-heterocycle aniline 3ag was prepared in low yield. Finally, the developed method is suitable for the late-stage arylation of drug-like molecules such as deacetyllinezolid (3ak). The meta-substituted anilines 3 are formed in a sequence of reactions shown in Scheme 6 [53]. Firstly, the reaction

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• gossypii, Tripomastigote Chagas, Tcruzi amastigota, Tcruzi epimastigota, Leishmania amazonensis, and Dengue larvicida. Keywords: dihydropyrimidinone/thione/selenone; green chemistry; in silico biological profile; multicomponent reaction (MCR); thiopyrandioxide; Introduction Multicomponent reactions (MCRs

• synthesis of new S-heterocyclic systems we tried to combine the broad synthetic potential of Biginelli condensation and high reactivity β-ketosulfone 1 (dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide) in various condensation reactions [14][15][16][17][18][19][20]. It was also worth mentioning that the thiopyran

• ). However, increasing acidity and using trifluoroacetic acid (Table 1, entry 17) did not improve the overall yield. We also tried microwave activation conditions since this is a known technique for reactions of this type [32], but unfortunately, we did not find any improvement in the yield (Table 1, entry

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

• Zsuzsanna Fehér,
• Dóra Richter,
• Gyula Dargó and
• József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

• , providing a cost-effective alternative to traditional catalytic methods. The immobilisation of organocatalysts offers the potential to increase catalyst reusability and efficiency in organic reactions. This article reviews the key parameters that influence the effectiveness of immobilised organocatalysts

• applications in organic chemistry. Keywords: asymmetric synthesis; catalyst recycling; heterogenisation; organocatalysis; solid support; Introduction Organocatalysts are small molecules that do not contain a metal atom in the reaction centre and are able to increase the speed of reactions. They have proven

• controllability of surface, geometry, and pore size makes silica-based materials sustainable and functionalisable supports for organocatalytic reactions [44]. The particle morphology of mesoporous silica can be tuned to various shapes, including spheres, tubes, and rods of various dimensions [45], by using a co

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

• reagents, and are widely used in organic synthesis. On the other hand, the use of isocyanides in reactions with heteroatom radicals is limited. However, the reaction of isocyanides with heteroatom radicals is a promising synthetic tool for the construction of nitrogen-containing organic molecules modified

• with a variety of heteroatoms. In this Perspective, we review the addition and cyclization reactions of heteroatom radicals with isocyanides and discuss the synthetic prospects of the reaction of isocyanides with heteroatom radicals. Keywords: aza-Bergman cyclization; heteroatom-mixed system; imidoyl

• ), but is also widely used in transition-metal-catalyzed carbonylation reactions [1][2]. However, carbon monoxide is a flammable gas with a wide explosive range, although colorless and odorless, and requires special care in handling due to its high toxicity. In addition, when carbon monoxide is used in a

Cage-like microstructures via sequential Ugi reactions in aqueous emulsions

• Rita S. Alqubelat,
• Yaroslava A. Menzorova and
• Maxim A. Mironov

Beilstein J. Org. Chem. 2024, 20, 2078–2083, doi:10.3762/bjoc.20.179

• Rita S. Alqubelat Yaroslava A. Menzorova Maxim A. Mironov Department of Technology for Organic Synthesis, Ural Federal University, Mira St. 19, Ekaterinburg, 620002, Russian Federation 10.3762/bjoc.20.179 Abstract Cage-like microstructures were obtained in two steps by sequential Ugi reactions

• sequential Ugi reactions, the first to form colloidal particles and the second to consolidate the Pickering emulsion structure. In both cases, the same technique was used: a mixture of hexamethylene diisocyanide and formalin in acetonitrile was added dropwise into an aqueous suspension or emulsion at a ratio

• application. Single droplets of the Pickering emulsion attached to a glass surface. Cage-like microstructure obtained via sequential Ugi reactions. AFM images of A) single domains and B) cross-linked CMC/chitosan polymer particles. Variations of microstructures obtained via sequential Ugi reactions. A) Cap

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• numerous other applications. The search for new and efficient syntheses of these heterocycles is therefore highly relevant. The modular concept of multicomponent reactions (MCR) has paved a broad alley to heteroaromatics. The advantages over traditional methods are the broader scope and increased

• efficiency of these reactions. In particular, traditional multistep syntheses of pyrazoles have considerably been extended by MCR. Progress has been made in the cyclocondensation of 1,3-dielectrophiles that are generated in situ. Limitations in the regioselectivity of cyclocondensation with 1,3-dicarbonyls

• ; one-pot reactions; pyrazole; Introduction Pyrazoles and 1,2-diazoles [1] have received considerable interest in the past years. Although they are rarely found in nature [2], their spectrum of biological activity is remarkably broad, leading to numerous applications in pharmaceutical chemistry [3][4

Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates

• Deepa Nair,
• Abhishek Tiwari,
• Banamali Laha and
• Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2024, 20, 2016–2023, doi:10.3762/bjoc.20.177

• starting materials for cascade/domino reactions. Curcumin is the key component present in turmeric and is responsible for its various biological activities. Turmeric has been used in many forms for potential health benefits and as a traditional spice for centuries [11]. Curcumin exhibits diverse biological

• reactions, especially as a Michael donor at the central methylene carbon, and Michael acceptor at the enone vinyl carbon. Therefore, it would be interesting to develop novel methodologies using curcumin and its non-natural analogs as key starting materials [24]. Because of its multifaceted reactive site

• , curcumin showcases its Michael donor–acceptor ability in different ways, such as simple Michael addition, [4 + 2] annulation, Michael addition followed by cyclization or one-pot multicomponent reactions (MCR), etc. (Scheme 1) [25]. In 2011, our group reported the reactivity of curcumin as a Michael donor

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

• Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

• versatile reagents in organic synthesis. They have for instance been frequently employed for the construction of azacycles through various cyclization protocols or cycloaddition reactions [6][7][8][9][10]. Early work in this field includes the well-known Fischer indole synthesis [11]. Additionally, they

• have been harnessed as valuable intermediates in Wolff–Kishner reduction reactions [12][13][14] or for the synthesis of various olefins via diazo or vinyllithium intermediates in the Bamford–Stevens reaction [15] and Shapiro reaction [16], respectively [17]. SAMP/RAMP ((S)/(R)-1-amino-2

• miscellaneous compounds. For reactions carried out under constant current electrolysis, the reported current applied (in A or mA) is depicted. Additionally, when possible, and for better accuracy, the current density (in mA·cm−2) has been calculated based on the size of the electrode portion immersed in the

Development of a flow photochemical process for a π-Lewis acidic metal-catalyzed cyclization/radical addition sequence: in situ-generated 2-benzopyrylium as photoredox catalyst and reactive intermediate

• Masahiro Terada,
• Zen Iwasaki,
• Ryohei Yazaki,
• Shigenobu Umemiya and
• Jun Kikuchi

Beilstein J. Org. Chem. 2024, 20, 1973–1980, doi:10.3762/bjoc.20.173

• unstable chemical species by controlling parameters such as flow velocity and mixing properties, and in some cases makes it possible to achieve reactions that are difficult to perform using batch chemistry [17][18][19][20][21]. In general, efficient two-phase mixing and heat transfer, as well as ease of

• , initiating further radical reactions through the formation of radical cations B. Nucleophilic arylmethyl radicals C, which are generated from radical cations B by desilylation, undergo an addition reaction with 2-benzopyrylium intermediates A, giving rise to the corresponding radical cation. Catalytic cycle

• ]. As expected, the use of the flow reaction system significantly increased yields, although the yields obtained in the reactions of substrates having an electron-donating methoxy group were low to moderate regardless of the substitution pattern (Table 2, entries 1, 2, and 6). Indeed, when a methoxy

Radical reactivity of antiaromatic Ni(II) norcorroles with azo radical initiators

• Siham Asyiqin Shafie,
• Ryo Nozawa,
• Hideaki Takano and
• Hiroshi Shinokubo

Beilstein J. Org. Chem. 2024, 20, 1967–1972, doi:10.3762/bjoc.20.172

• LUMO (Figure 1) [11]. Reactions with nucleophiles (Nu) proceed with perfect regioselectivity at the distal β-position relative to the meso-position [12][13][14][15]. On the other hand, reactions with electrophiles (El) also occur preferentially at the β-positions, but the regioselectivity depends on

• ]. Moreover, the ring-expansion or ring-opening reactions of Ni(II) norcorroles are induced by an activated zwitterionic intermediate [22], oxidants [23][24], and carbenes [25][26]. During the last decade, the various reactivities of Ni(II) norcorroles have been elucidated. However, the reaction with radical

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

• Liubov V. Sokolenko,
• Taras M. Sokolenko and
• Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

• 1,2-difluoroethylene (HFO-1132). The major routes for the preparation of the E- and Z-isomer of HFO-1132 are reviewed, along with the chemistry in radical, nucleophilic, and electrophilic reactions. Keywords: 1,2-difluoroethylene; fluorinated monomers; HFO-1132; hydrofluoroolefins; radical reactions

• converted into polyfluorinated olefins RFCF=CFH by HI elimination. Cyclization reactions Carbocyclizations: A series of articles devoted to structural investigations of 1,2-difluorocyclopropanes was published [96][97][98]. For this purpose, cis- and trans-1,2-difluorocyclopropanes were synthesized by liquid

• products were separated by column chromatography and characterized. Heterocyclizations–photochemical [2 + 2]- and [2 + 4]-cycloaddition reactions: The formation of oxetanes as a result of photochemical cycloaddition of fluoroketones or fluoroaldehydes and 1,2-difluoroethylene was previously described by

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

• Pengcheng Lu,
• Luis Juarez,
• Paul A. Wiget,
• Weihe Zhang,
• Krishnan Raman and
• Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

• Discussion We commenced our studies by investigating yields of N1- and N2-substituted products of conventional indazole alkylation reactions using our model substrate methyl 5-bromo-1H-indazole-3-carboxylate (6) and confirmed structures of the corresponding N1-substituted and N2-substituted products. In

• reactions with compound 6 afforded the N1-substituted indazole analogs 15a–q with excellent yields (>90%), except for 15m, which failed to form after multiple attempts likely due to an instability of the electrophile 14m under optimized conditions (conditions A: 1.5 equiv tosylate, 1.0 equiv 6, 2.0 equiv

• isolated in >99% yield under conditions B albeit with low conversion. Both conditions provided >98:2 regioselectivity for their respective major products as determined by LC–MS. We again turned to DFT calculations to explore the mechanisms of these reactions and found very similar results to the parent

A new platform for the synthesis of diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions

• Vitor A. S. Almodovar and
• Augusto C. Tomé

Beilstein J. Org. Chem. 2024, 20, 1933–1939, doi:10.3762/bjoc.20.169

• synthesis of highly fluorescent DPP derivatives through straightforward nucleophilic aromatic substitution reactions with thiols and phenols. These nucleophilic substitutions occur at room temperature and manifest a remarkable selectivity for the 4-position of the pentafluorophenyl groups. Both symmetrical

• -di(het)aryl groups via Suzuki–Miyaura [26][27][28] or Sonogashira [29][30][31] reactions. In this study, we report a straightforward method to obtain a diverse array of N-substituted DPP derivatives through a two-step process. Firstly, the N-alkylation of Pigment Red 254 (DPP 1) is achieved using

• generating new DPP derivatives through nucleophilic aromatic substitution reactions with thiols and phenols. The main objective of this study was to employ the N,N’-bis(pentafluorobenzyl)-DPP 2 as an electrophile and investigate its reactivity with thiols and phenols (Scheme 1). All SNAr reactions were

Negishi-coupling-enabled synthesis of α-heteroaryl-α-amino acid building blocks for DNA-encoded chemical library applications

• Matteo Gasparetto,
• Balázs Fődi and
• Gellért Sipos

Beilstein J. Org. Chem. 2024, 20, 1922–1932, doi:10.3762/bjoc.20.168

• ]. The success of this technology ultimately relies on the quality and diversity of the libraries. DEL synthesis must employ DNA-compatible reactions; hence it operates under a limited set of conditions [4][5]. DELs are typically produced via split-and-pool combinatorial chemistry methods. Using

• ][28]. However, the selectivity of these photoredox reactions is driven by the structural properties of the heteroaromatic ring. During the preparation of this article, the Meggers group published an outstanding enantioselective iron-catalyzed α-amination pathway (Scheme 1b) [29]. The method is widely

• unaffected by the presence of light (see pages 5 and 6 in Supporting Information File 1). In the case of indazoles, increased reaction rates were observed in the presence of light, but the overall yield was the same for the dark and irradiated experiments. Although these reactions are typically complete

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

• Ze-Nan Hu,
• Yan-Hui Wang,
• Jia-Bing Wu,
• Ze Chen,
• Dou Hong and
• Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

• - or 4-substituted isoquinolinone derivatives with excellent chemoselectivity. These interesting findings led us to investigate the reaction mechanism. To gain insight into the mechanism and chemoselectivity of the reactions above, we performed a control experiment. With acetonitrile as the solvent, a

Novel oxidative routes to N-arylpyridoindazolium salts

• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2024, 20, 1906–1913, doi:10.3762/bjoc.20.166

• involvement of the amines’ lone pair in the new 14-e aromatic system (Scheme 2). One of the possible functionalities of the new compounds may be the utility of the charged aromatic fragment as an efficient leaving group in the SN(Ar) reactions, similarly to dibenzothiophenium triflates that have been recently

Electrochemical radical cation aza-Wacker cyclizations

• Sota Adachi and
• Yohei Okada

Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165

• step to driving bond formation and/or cleavage. Therefore, the discovery of new modes for activation leads to reaction advancements. Electrochemical [1][2][3][4][5] and photochemical [6][7][8][9][10] reactions that induce single-electron reduction and oxidation are widely used in modern synthetic

• ). For example, Moeller reported electrochemical reactions under basic conditions, which were proposed to proceed via radicals [16][17][18]. Xu also reported electrochemical reactions via radicals, which were generated through proton-coupled electron transfer [19]. On the other hand, Yoon reported

• photochemical reactions under acidic conditions, which were proposed to proceed via radical cations [20]. Since electrochemical and photochemical aza-Wacker cyclizations can offer ring systems that are difficult to construct through state-of-the-art palladium-catalyzed methods, the mechanistic understanding of

Access to 2-oxoazetidine-3-carboxylic acid derivatives via thermal microwave-assisted Wolff rearrangement of 3-diazotetramic acids in the presence of nucleophiles

• Ivan Lyutin,
• Vasilisa Krivovicheva,
• Grigory Kantin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 1894–1899, doi:10.3762/bjoc.20.164

• the lower stability of the less-substituted β-lactam derivatives under thermolysis conditions. Additional alkyl substituents sterically shield the ring and prevent an unwanted nucleophilic attack leading to product degradation. In reactions with alcohols and mercaptans, the corresponding esters 3k–n,r

• -generated ketene, previously described using carbocyclic diazodiketones [35] were also unsuccessful. Of the diazotetramic acids, only the spiro adamantane derivative 1m was not able to form the desired β-lactam. These reactions gave complex mixtures of unidentified products. The benzyl esters 3k and 3n were

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

• achieved during the last five years, and classifies them into five categories: synthetic methods, building blocks, scaffolds, biological activities and physical properties. Keywords: Groebke–Blackburn–Bienaymé reaction; multicomponent reactions; heterocycles; imidazo[1,2-a]pyridines; isocyanides

• encountered by the reaction until 2019 was far from being at its peak, in fact during the last 5 years about 70 new original works have been published, and it is therefore worth analyzing what are the new features of this, now, mature reaction. Among isocyanide [2] based multicomponent reactions, the GBB

• reaction can be considered the third in importance after Ugi [3] and Passerini [4] ones, and, as the two venerable reactions, is an α-addition of an electrophile and a nucleophile to an isocyanide, followed by a suitable rearrangement, as depicted in Scheme 1. Compared with the Passerini and Ugi reactions

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

• Ivana Weisheitelová,
• Radek Cibulka,
• Marek Sikorski and
• Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

• (All) and also 5-deazaflavins (dFl) and 5-deazaalloxazines (dAll), where the N(5) atom of the isoalloxazine/alloxazine core is replaced by a C–H moiety (Figure 1A). In particular, 5-deazaflavins have generated considerable interest from scientists to study flavin-catalysed reactions in enzymatic and

• 2, as demonstrated in our previous studies with 5-aryldeazaflavins 1 [14][15][16][17][18]. Multicomponent reactions (MCRs) remain a powerful strategy in synthetic organic chemistry due to their widespread applications in drug discovery. By offering significant advantages over conventional, linear

• /alloxazine photoredox catalysis [9][14][15][16][17][18][19], 7-methoxyderivatives should also be considered due to their absorption closer to the visible light region. This allows longer wavelength LEDs with lower energy photons to be applied, potentially contributing to avoiding undesired reactions [14][15

Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity

• Moisés Alejandro Alejo Hernandez,
• Katia Pamela Villavicencio Sánchez,
• Rosendo Sánchez Morales,
• Karla Georgina Hernández-Magro Gil,
• David Silverio Moreno-Gutiérrez,
• Eddie Guillermo Sanchez-Rueda,
• Yanet Teresa-Cruz,
• Brian Choi,
• Armando Hernández Garcia,
• Alba Romero-Rodríguez,
• Oscar Juárez,
• Siseth Martínez-Caballero,
• Mario Figueroa and
• Corina-Diana Ceapă

Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159

• times dehydrated was identified. Cyclization reactions introduced thioether cross-links between dehydrated Thr/Ser residues and specific cysteine thiol groups. However, due to identical masses of dehydrated linear peptides (lacking thioether rings) and cyclic forms (containing Dhb and Dha rings), a

• peptidase domain, was mixed with samples of CloA1 and CloA2A at a 1:5 molar ratio within a reaction buffer composed of 50 mM HEPES at pH 7.0, 150 mM NaCl, and 5 mM DTT. Cofactors were added as indicated, with the following concentrations: 0.5 mM ATP and 1 mM MgCl2. The reactions were incubated at 4 °C for

Chiral bifunctional sulfide-catalyzed enantioselective bromolactonizations of α- and β-substituted 5-hexenoic acids

• Sao Sumida,
• Ken Okuno,
• Taiki Mori,
• Yasuaki Furuya and
• Seiji Shirakawa

Beilstein J. Org. Chem. 2024, 20, 1794–1799, doi:10.3762/bjoc.20.158

• enantioselectivity. The reactions of α,α-dialkyl-5-hexenoic acids 2e and 2f gave the corresponding bromolactonization products 3e and 3f with moderate enantioselectivities. The present catalytic method could also be applied to the asymmetric synthesis of spirolactones [37][38][39]. For example, α-spiro-δ-lactone

• -hexenoic acids 2, β-substituted substrates 2j–n were submitted to the present catalytic system. As a result of these asymmetric reactions, β,β-dialkyl-δ-valerolactones 3j–k and β-spiro-δ-lactones 3l–n were obtained in good levels of enantioselectivity. The reaction of 2-allylbenzoic acid 2o as a related

• product 3a for further transformations. Comparable yield and enantioselectivity were observed relative to those of the smaller-scale reaction (0.1 mmol scale, Scheme 4). The bromomethyl group in 3a readily undergoes nucleophilic substitution reactions, leading to the formation of optically active δ

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

• Samuel M. G. Dearman,
• Xiang Li,
• Yang Li,
• Kuldip Singh and
• Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

• be the best reagent for preparing bicyclic iodine(V) difluoride 6, this route was first investigated for the oxidative fluorinations of hypervalent iodine(III) amides 11a and 11b (Scheme 3). Unfortunately, these reactions did not work and difluoro(aryl)-λ5-iodanes 7a and 7b were not produced. Togni’s

• protocol using TCCA (4 equivalents) and KF (6 equivalents) was then applied to both bicyclic iodine(III) amides 11a and 11b, but these reactions also failed to form either difluoroiodane 7a or 7b. Following the successful preparation and isolation of difluoroiodane 6, we investigated its ability to

• (blue line), dry CDCl3 with 2.4 equivalents of dry pyridine (green line), and dry CDCl3 (red line). Order of hydrolytic stability for the four hypervalent iodine(V) fluorides. Examples of fluorination using hypervalent iodine(III) reagents 1 and 2. Preparations and reactions of hypervalent iodine(V