Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

• Yujun Pang,
• Jinglan Yan,
• Nawaf Al-Maharik,
• Qian Zhang,
• Zeguo Fang and
• Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

• target products in good to excellent yields. Mechanistic studies revealed that the reaction proceeds via a radical pathway. Keywords: cyclization; difluoromethylation; hypervalent iodine; polycyclic imidazole; visible light; Introduction Organofluorine compounds continue to play important roles in

• reaction (Table 1). Employing PIDA as the promoter, THF as the solvent, and 72 W white LED as the light source, the desired product 3a formed in 85% isolated yield at room temperature (Table 1, entry 1). We found that the hypervalent iodine reagent was of significant importance for the present

Recent advances in organocatalytic atroposelective reactions

• Henrich Szabados and
• Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

• Beatriz Dedeiras,
• Catarina S. Caldeira,
• José C. Cunha,
• Clara S. B. Gomes and
• M. Manuel B. Marques

Beilstein J. Org. Chem. 2024, 20, 3281–3289, doi:10.3762/bjoc.20.272

• Beatriz Dedeiras Catarina S. Caldeira Jose C. Cunha Clara S. B. Gomes M. Manuel B. Marques LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA FCT , 2829-516 Caparica, Portugal 10.3762/bjoc.20.272 Abstract The reactivity of our recently disclosed hypervalent iodine

• . A plausible mechanism is proposed, suggesting a possible radical pathway. Keywords: electrophilic amination; hypervalent iodine reagents; sulfinamide; sulfonamide; Introduction Iodine(III) compounds, known as λ3-iodanes, have been extensively applied in organic synthesis. Although initially used

• distorted T-shaped geometry, consistent with previously reported N–bound hypervalent iodine reagents. Additionally, the N–I bond distance is 2.0454(5) Å, which aligns with our previously reported values [4]. The two aromatic rings are nearly coplanar, exhibiting a dihedral angle of 0.7(3)°. All other bond

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

• Radell Echemendía,
• Carlee A. Montgomery,
• Fabio Cuzzucoli,
• Antonio C. B. Burtoloso and
• Graham K. Murphy

Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263

• 10.3762/bjoc.20.263 Abstract A novel study on the hypervalent iodine-mediated polyfluoroalkylation of sulfoxonium ylides was developed. Sulfoxonium ylides, known for their versatility and stability, are promising substrates for numerous transformations in synthetic chemistry. This report demonstrates the

• reactants. Finally, DFT calculations provided insights about the mechanism of this transformation, which strongly suggest that an SN2 reaction is operative. Keywords: alkylation; DFT calculations; fluorine chemistry; hypervalent iodine; sulfoxonium ylide; sulphur ylides; Introduction Introducing fluorine

• research groups recently reported the α-arylation between sulfoxonium ylides and diaryliodonium salts [33], and encouraged by this precedent, we envisioned that the chemistry between sulfoxonium ylides and hypervalent iodine compounds might be ripe for further exploitation. The trifluoroethyliodonium salt

Hypervalent iodine-mediated intramolecular alkene halocyclisation

• Charu Bansal,
• Oliver Ruggles,
• Albert C. Rowett and
• Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258

• Charu Bansal Oliver Ruggles Albert C. Rowett Alastair J. J. Lennox University of Bristol, School of Chemistry, Bristol, BS8 1TS, UK 10.3762/bjoc.20.258 Abstract The chemistry of hypervalent iodine (HVI) reagents has gathered increased attention towards the synthesis of a wide range of chemical

• ; heterocycles; hypervalent iodine; oxidation; Introduction Halogenated carbocyclic and heterocyclic compounds are present in many active pharmaceutical ingredients [1][2]. The intramolecular halocyclisation of alkenes mediated by HVI(III) reagents allow access to a range of halogenated cyclic scaffolds in a

• this review aims to fill. The synthetic uses of HVI reagents [14][15][16], their involvement in heterocycle synthesis [17][18][19], and alkene functionalisation [20][21], have each been well-reviewed elsewhere. Review Hypervalent iodine-mediated fluorocyclisation Fluorine can substantially improve the

Advances in radical peroxidation with hydroperoxides

• Oleg V. Bityukov,
• Pavel Yu. Serdyuchenko,
• Andrey S. Kirillov,
• Gennady I. Nikishin,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

• intermediate C with tert-butylperoxy radical B leads to the target product 38. Pathway II involves the oxidation of TBAI with TBHP to form hypervalent iodine compounds D and E. The reaction of species E with substrate 37 leads to the formation of intermediate F, which interacts with TBHP to yield product 38

Structure and thermal stability of phosphorus-iodonium ylids

• Andrew Greener,
• Stephen P. Argent,
• Coby J. Clarke and
• Miriam L. O’Duill

Beilstein J. Org. Chem. 2024, 20, 2931–2939, doi:10.3762/bjoc.20.245

• Andrew Greener Stephen P. Argent Coby J. Clarke Miriam L. O'Duill School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK 10.3762/bjoc.20.245 Abstract Hypervalent iodine(III) reagents have become indispensable tools in organic synthesis, but gaps remain in the

• and potential decomposition pathways will enable the future design and development of new reagents. Keywords: hypervalent iodine; reagent development; structural analysis; thermal stability; thermogravimetric analysis; Introduction Hypervalent iodine(III) reagents have experienced a renaissance in

• enable access to chemical motifs that are difficult to synthesise using traditional approaches. However, gaps remain in the functionality they can transfer. Specifically, unstabilised alkyl groups are still underrepresented. For the development of new hypervalent iodine reagents to bridge this gap, it is

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

• arylation; rearrangement reaction; Introduction The chemistry of hypervalent iodine compounds is well-established and they are prevalent as oxidants and electrophilic reagents in organic conversions [1][2][3]. They have gained significant attention due to their high reactivity and ability to carry out

• various useful transformations under mild, eco-friendly reaction conditions [4][5][6][7][8][9][10][11]. Various review articles [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] and books [27][28] have appeared on the chemistry of hypervalent iodine compounds. In the past two decades

• , diaryliodonium salts (DAIS), a versatile category of hypervalent iodine compounds, have seen significant progress in hypervalent iodine chemistry. Their efficiency and environmentally friendly characteristics have positioned DAIS as next-generation arylation reagents [29][30]. Other than aromatic electrophiles

Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

• Smaher E. Butt,
• Konrad Kepski,
• Jean-Marc Sotiropoulos and
• Wesley J. Moran

Beilstein J. Org. Chem. 2024, 20, 2455–2460, doi:10.3762/bjoc.20.209

• Pierre Angot, 64053 Pau Cedex 09, France School of Pharmacy and Bioengineering, Keele University, Keele, Staffordshire ST5 5JX, United Kingdom 10.3762/bjoc.20.209 Abstract A change in mechanism was observed in the hypervalent iodine-mediated cyclization of N-alkenylamides when the carbon chain between

• , reaction conditions were developed, and the scope of this cyclization studied. Keywords: cyclization; DFT; hypervalent iodine; mechanism; proline; Introduction Proline is one of the 20 DNA-encoded proteinogenic amino acids that are essential to life [1][2]. In addition, the pyrrolidine core is present in

• enantioselective conjugate addition to α,β-unsaturated pyroglutamic acid derivatives followed by deoxygenation [10], and the enantioselective organocatalytic reaction between 2-acylaminomalonates and α,β-unsaturated aldehydes [11][12]. The development of new synthetic methods using hypervalent iodine reagents has

Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt

• Dominik L. Reinhard,
• Anna Schmidt,
• Marc Sons,
• Julian Wolf,
• Elric Engelage and
• Stefan M. Huber

Beilstein J. Org. Chem. 2024, 20, 2401–2407, doi:10.3762/bjoc.20.204

• . Finally, the potential as halogen-bonding activator was benchmarked in solution in the gold-catalyzed cyclization of a propargyl amide. Keywords: diaryliodonium; gold catalysis; halogen bonding; hypervalent iodine; non-covalent interactions; Introduction The compound class of diaryliodonium (DAI) salts

Hydrogen-bond activation enables aziridination of unactivated olefins with simple iminoiodinanes

• Phong Thai,
• Lauv Patel,
• Diyasha Manna and
• David C. Powers

Beilstein J. Org. Chem. 2024, 20, 2305–2312, doi:10.3762/bjoc.20.197

• Phong Thai Lauv Patel Diyasha Manna David C. Powers Department of Chemistry, Texas A&M University, College Station TX, 77843, USA 10.3762/bjoc.20.197 Abstract Iminoiodinanes comprise a class of hypervalent iodine reagents that is often encountered in nitrogen-group transfer (NGT) catalysis. In

• the potential for chemical non-innocence of fluorinated alcohol solvents in NGT catalysis. Keywords: aziridination; electrochemistry; H-bond activation; hypervalent iodine; nitrene transfer; Introduction Hypervalent iodine reagents find widespread application in selective oxidation chemistry due to

• ]. Iminoiodinanes (ArI=NR) are a subclass of hypervalent iodine reagents that function as nitrene equivalents in synthesis [5][6]. The direct reaction of iminoiodinanes with olefins, which could be envisioned to give rise to aziridines directly, is typically not observed and thus families of transition metal

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

• esters are tolerated in the method [113]. Starting from enaminone 86 functionalization, the hypervalent iodine compound 87 facilitates the introduction of a difluoromethanesulfonyl group in the copper(I) bromide-mediated consecutive three-component synthesis of difluoromethanesulfonyl-functionalized

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

• isoquinolinone derivatives. The method provides highly chemoselective access to 3- or 4-substituted isoquinolinone derivatives by reacting o-alkenylbenzamide derivatives with PISA in either acetonitrile or wet hexafluoro-2-isopropanol. Keywords: annulation; C–H amination; hypervalent iodine reagent; iodine(III

• option for the preparation of isoquinolinone derivatives. In 2020, two reports have been published on the conversion of alkyne-tethered N-alkoxybenzamides to isoquinolinones by intramolecular oxidative annulation, either electrochemically or using the hypervalent iodine reagent phenyliodine(III

• zwitterionic water-soluble hypervalent iodine reagent (phenyliodonio)sulfamate (PISA). In water, PISA is strongly acidic, and the pH value can reach 2.05 in a saturated aqueous solution. With PISA, various indoles have been synthesized via C–H amination of 2-alkenylanilines involving an aryl migration

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

• investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild and efficient route using Selectfluor to deliver hypervalent iodine(V

• ; fluorobenziodoxoles; halogen bonding; hypervalent iodine; Selectfluor; Introduction An important strategy in the drug discovery process is the incorporation of fluorine into biologically active molecules because fluorine can improve bioactivity and pharmacokinetic properties [1]. Consequently, 22% of all small

• -molecule drugs contain at least one fluorine atom [2]. Hypervalent iodine(III) fluorides, such as difluoroiodotoluene 1 and fluoroiodane 2, have been key to the development of numerous, new synthetic procedures for C–F bond formation over the last decade. Since difluoroiodotoluene 1 has low chemical

Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)

• Hiwot M. Tiruye,
• Solon Economopoulos and
• Kåre B. Jørgensen

Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153

• radical (potassium nitrosodisulfonate) [13] or catalytic systems like methyltrioxorhenium(VII) (MeReO3) [14] and 2-iodobenzenesulfonic acids (IBS)/Oxone® [15] led to either p-quinones or o-quinones, depending on the substituents in the para-position to the hydroxy group. Recently, hypervalent iodine

Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ³-iodanes

• Thomas J. Kuczmera,
• Pim Puylaert and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 1677–1683, doi:10.3762/bjoc.20.149

• )iodane is proposed as the reactive intermediate. Keywords: alcohol oxidation; hypervalent iodine; N-heterocycles; Introduction The oxidation of alcohols to aldehydes and ketones is an essential transformation in organic chemistry [1][2]. Generating aldehydes is particularly challenging as they are

• oxidants in combination with transition-metal catalysts. Metal-free methods employ chlorodimethylsulfonium compounds as the reactive species and have gained great popularity under the name Swern oxidation or the Corey–Kim oxidation [11]. Hypervalent iodine compounds have also been studied and are well

• -iodanes have drawbacks, in particular low solubility and moisture sensitivity [11]. Hypervalent iodine compounds in a lower oxidation state (λ3-iodanes), such as iodosobenzene (PhIO)n or phenyliodine(III) diacetate (PIDA) have been reported in alcohol oxidations but they often result in overoxidation to

Divergent role of PIDA and PIFA in the AlX₃ (X = Cl, Br) halogenation of 2-naphthol: a mechanistic study

• Kevin A. Juárez-Ornelas,
• Manuel Solís-Hernández,
• Pedro Navarro-Santos,
• J. Oscar C. Jiménez-Halla and
• César R. Solorio-Alvarado

Beilstein J. Org. Chem. 2024, 20, 1580–1589, doi:10.3762/bjoc.20.141

• halogenation via PhIX2. Keywords: aromatic bromination; aromatic chlorination; density functional theory (DFT); hypervalent iodine; iodine(III); Introduction Hypervalent iodine(III) reagents have gained attention as strong oxidants with a low toxicity [1][2][3][4][5][6][7][8] and due to the ability to mimic

• . In contrast to the suggested traceroute where the chlorine or bromine atom is attached to the hypervalent iodine center of the plausible reagent PhIX2 (X = Cl, Br), our new protocol opens up a broad path for the reaction through different halogenating species. For a deeper understanding of these

• 0 kcal/mol for more clarity. Herein, one chlorine atom is transferred from aluminum to the hypervalent iodine(III) center through six-membered-ring transition state TS1–Cl (ΔG‡ = 9.7 kcal/mol, selected bond lengths 2.76, 1.22, 1.27, 1.78, 2.60, and 2.86 Å for I–O, O–C, C–O, O–Al, Al–Cl, and Cl–I

Benzylic C(sp³)–H fluorination

• Alexander P. Atkins,
• Alice C. Dean and
• Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

• is subsequently oxidised to Mn(V)-oxo species II by hypervalent iodine oxidant PhIO. This can perform a HAT from the benzylic substrate, in turn generating a benzylic radical and Mn(IV)-hydroxy species III. Ligand exchange with the fluoride source affords complex IV, which performs FAT with the

• substituents on the aryl group benefitted from fewer HF equivalents and the addition of silver fluoride. A follow-up report showed that only minor alterations to the conditions were needed to make the process amenable to the use of [18F]KF, facilitating radiofluorination [81]. Both reports used hypervalent

• iodine as a super-stoichiometric oxidant. The catalyst system has precedent for also facilitating oxygenation reactions [82], which was observed as a competing pathway under these conditions. The catalytic cycle proposed by the authors begins at resting state I (Figure 31), which is generated in situ and

Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide

• Christopher Mairhofer,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1510–1517, doi:10.3762/bjoc.20.135

• addition, the recent years have seen remarkable progress in utilizing electrophilic azide-transfer reagents, i.e., hypervalent iodine-based compounds, for (asymmetric) α-azidations [16][17][18][19][20][21][22][23]. Besides these valuable approaches, which either require appropriate pre-functionalization of

• mechanistic scenario. Application scope. Proof-of-concept for the analogous oxidative α-nitration. Optimization of the α-azidation of β-ketoester 1aa. Control experiments using different hypervalent iodine speciesa. Supporting Information Supporting Information File 24: Full experimental and analytical

Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl₂ and NH₄SCN/KSeCN

• Jialiang Wu,
• Haofeng Shi,
• Xuemin Li,
• Jiaxin He,
• Chen Zhang,
• Fengxia Sun and
• Yunfei Du

Beilstein J. Org. Chem. 2024, 20, 1453–1461, doi:10.3762/bjoc.20.128

• Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, China 10.3762/bjoc.20.128 Abstract A series of 4-thio/seleno-cyanated pyrazoles was conveniently synthesized from 4-unsubstituted pyrazoles using NH4SCN/KSeCN as thio/selenocyanogen sources and PhICl2 as the hypervalent iodine

• , we have accomplished the synthesis of a series of C-4 thio/selenocyanated pyrazoles via a hypervalent iodine-mediated electrophilic thio/selenocyanation approach under mild reaction conditions. Furthermore, the obtained S/SeCN-containing pyrazoles can be converted to S/SeCF3- and S/SeMe-containing

Predicting bond dissociation energies of cyclic hypervalent halogen reagents using DFT calculations and graph attention network model

• Yingbo Shao,
• Zhiyuan Ren,
• Zhihui Han,
• Li Chen,
• Yao Li and
• Xiao-Song Xue

Beilstein J. Org. Chem. 2024, 20, 1444–1452, doi:10.3762/bjoc.20.127

• , University of Chinese Academy of Sciences, Shanghai 200032, P. R. China, School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, P. R. China 10.3762/bjoc.20.127 Abstract Although hypervalent iodine(III) reagents have

• ; machine learning; Introduction Hypervalent iodine reagents are increasingly gaining attention in the fields of organic synthesis and catalysis due to their environmental benefits, accessibility, and cost-efficiency [1][2][3][4][5][6][7][8][9][10][11]. Over the last three decades, a series of cyclic

• hypervalent iodine(III) reagents has been developed [12][13][14][15][16][17] (Figure 1), including the well-known Zhdankin reagents [13] and Togni reagents [14]. These reagents are popularly used as electrophilic group transfer reagents [18][19] in a variety of reactions, such as C–H functionalization [20][21

Hypervalent iodine-catalyzed amide and alkene coupling enabled by lithium salt activation

• Akanksha Chhikara,
• Fan Wu,
• Navdeep Kaur,
• Prabagar Baskaran,
• Alex M. Nguyen,
• Zhichang Yin,
• Anthony H. Pham and
• Wei Li

Beilstein J. Org. Chem. 2024, 20, 1405–1411, doi:10.3762/bjoc.20.122

• .20.122 Abstract Hypervalent iodine catalysis has been widely utilized in olefin functionalization reactions. Intermolecularly, the regioselective addition of two distinct nucleophiles across the olefin is a challenging process in hypervalent iodine catalysis. We introduce here a unique strategy using

• simple lithium salts for hypervalent iodine catalyst activation. The activated hypervalent iodine catalyst allows the intermolecular coupling of soft nucleophiles such as amides onto electronically activated olefins with high regioselectivity. Keywords: amide coupling; hypervalent iodine catalysis

• ; lithium salt activation; olefin oxyamination; oxazoline; Introduction Hypervalent iodine(III) reagents, also known as λ3–iodanes, have been well established and used in organic synthesis for the past decades [1][2][3][4][5]. The pioneering works of Fuchigami and Fugita, Ochiai, Kita, and later the

Oxidative hydrolysis of aliphatic bromoalkenes: scope study and reactivity insights

• Amol P. Jadhav and
• Claude Y. Legault

Beilstein J. Org. Chem. 2024, 20, 1286–1291, doi:10.3762/bjoc.20.111

• utilizing a hypervalent iodine-catalyzed oxidative hydrolysis reaction. This catalytic process provides both symmetrical and unsymmetrical dialkyl bromoketones with moderate yields across a broad range of bromoalkene substrates. Our studies also reveal the formation of Ritter-type side products by an

• alternative reaction pathway. Keywords: bromoalkenes; bromoketones; hypervalent iodine; oxidative hydrolysis; Ritter-type; Introduction Organic synthesis heavily relies on oxidative transformations to facilitate chemical reactions. One popular method for achieving these transformations is using redox-active

• metals, inspired by Nature's metalloproteins. However, using toxic and expensive metals is not always practical, making alternative oxidative methodologies more appealing. Enter hypervalent iodine reagents – a leading metal-free choice for oxidation reactions. These robust and low-toxicity reagents have

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

• Naoki Miyamoto,
• Daichi Koseki,
• Kohei Sumida,
• Elghareeb E. Elboray,
• Naoko Takenaga,
• Ravi Kumar and
• Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

• . This method allows for the hybridization of complex bioactive and fluorescent-labeled carboxylic acids with diaryliodonium(III) salts. Keywords: auxiliary ligand; diaryliodonium(III) salts; hybridization; hypervalent iodine; organocarboxylates; Introduction Hypervalent iodine compounds are an

• (TFE, Scheme 2B) [21]. Our group previously reported the synthesis of diaryliodonium(III) salts by combining hypervalent iodine(III) reagents with electron-rich arenes in fluoroalcohol solvents, such as TFE or 1,1,1,3,3,3-hexafluoro-2-propanol [21][22]. These solvents stabilize the cationic

• counterion exchange step. By employing TMP as an auxiliary aryl group, we have successfully achieved the reaction between the hypervalent iodine compounds (ArI(OAc)2 or ArIO) and 1,3,5-trimethoxybenzene in the presence of organocarboxylic acid under mild conditions. This process was completed in

Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles

• Jun Kikuchi,
• Roi Nakajima and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2024, 20, 891–897, doi:10.3762/bjoc.20.79

• group in the product can be leveraged as a versatile synthetic handle, allowing for the preparation of hitherto inaccessible types of densely functionalized N-vinylazoles. Keywords: alkynes; azoles; cross-coupling; hypervalent iodine; Introduction N-Functionalized azoles are prevalent in bioactive