N-Boc-α-diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N–H insertion reaction

• Grigory Kantin,
• Pavel Golubev,
• Alexander Sapegin,
• Alexander Bunev and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 1841–1848, doi:10.3762/bjoc.19.136

• α-bromo (α-oxysulfonyl) glutarimide (3, Scheme 1, route B). Although the first approach has readily available starting reagents, a simple synthesis process, and gives generally high yields, it is restricted in terms of the type of heterocycle that can be assembled (primarily cyclic imides and

Selectivity control towards CO versus H₂ for photo-driven CO₂ reduction with a novel Co(II) catalyst

• Lisa-Lou Gracia,
• Philip Henkel,
• Olaf Fuhr and
• Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

• Supporting Information File 1). The redox properties of 1 were investigated using cyclic voltammetry in a DMA solution with 0.1 M tetrabutylammonium hexafluorophosphate (TBAPF6) as the supporting electrolyte (Table 1). The concentration of the analyte was 5 mM. Only the cathodic scan resulted in a rich

• ), respectively. A more intense current arises with the third redox process occurring at −2.52 V, which could be assigned to the reduction localized on the ligand (compare with the cyclic voltammogram in Supporting Information File 1, Figure S8). We investigated the electrochemical properties also under a CO2

• -centered d–d transitions. Cyclic voltammetry of complex 1 in 0.1 M TBAPF6 solution of (a) DMA and (b) DMA/TEOA 5:1 (v/v). Black curves are registered under Ar and red curves are recorded under CO2 atmosphere. A glassy-carbon disk was used as the working electrode and the internal references used are (a

Unprecedented synthesis of a 14-membered hexaazamacrocycle

• Anastasia A. Fesenko and
• Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

• ., vitamin B12, chlorophyll, metalloproteins, cyclic peptides, etc). PAMs themselves and their metal complexes exhibit various useful properties [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31], particularly, they possess a wide range of biological activities and are used as contrast

• synthesis of novel PAMs with interesting properties is of great importance. Recently, we developed some approaches to 14-membered cyclic bis-semicarbazones [32][33][34][35] and bis-thiosemicarbazone [36], namely 7,14-dimethyl-1,2,4,8,9,11-hexaazacyclotetradeca-7,14-diene-3,10-diones and -3,10-dithiones. The

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• azomethine nitrogen N1 as H-acceptor is observed, which originates six-membered cyclic motifs with a graph-set (6) [39]. The hydrogen atom is closer to O1 than to N1, indicating that the preferred protonation site is the former, as can be observed at the Fourier difference maps (Figure S1A and S1B in

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

• Xiaofeng Zhang,
• Xiaoming Ma and
• Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

• group on the α-carbon atom are semi-stabilized (Scheme 1) [16]. The B1-type AMYs can be generated from the decarboxylative condensation of aldehydes with α- and N-dialkylglycines or from cyclic amino acids (such as proline) [31][32][33], while AMYs of type B2 are accessible through the decarboxylative

• (such as C60/C70 fullerenes) [56][57][58]. Other than amino esters and amino acids shown in Scheme 1, cyclic amines can also react with arylaldehydes to form B1-type semi-stabilized AMYs. In this context, the Seidel group reported the reactions of pyrrolidines 5 with arylaldehydes for the formation of

• AMYs B1 which then were reacted with nucleophiles to form C–H-functionalized pyrrolidines or subjected to the 1,3-dipolar cycloaddition with olefins to afford bicyclic compounds (Scheme 2A and B) [59][60]. We employed cyclic amines for the synthesis of spirooxindole-pyrrolidines 7a or 7b in good

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• optoelectronic devices. The electrochemical behavior of TPECNz was analyzed by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) in CH2Cl2 containing 0.1 M n-Bu4NPF6 as a supporting electrolyte. As illustrated in Figure 5b, the molecule shows multiple quasi-reversible oxidation and reduction

• illumination). a) DSC and TGA thermograms measured at a heating rate of 10 °C min−1 under N2 flow. b) Cyclic voltammogram (CV) and differential pulse voltammogram (DPV) analyzed in dry CH2Cl2 at a scan rate of 50 mV s−1 under an argon atmosphere (insert: HOMO/HOMO−1/LUMO orbitals). a) Schematic structure of

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

• Swagat K. Mohapatra,
• Khaled Al Kurdi,
• Samik Jhulki,
• Georgii Bogdanov,
• John Bacsa,
• Maxwell Conte,
• Tatiana V. Timofeeva,
• Seth R. Marder and
• Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

• crystallographically characterized. Electrochemistry The 1+, 1H, and 12 species were investigated using cyclic voltammetry in THF/0.1 M Bu4NPF6 at a scan rate of 50 mV s−1. The voltammograms (shown for one series of compounds in Figure 6) were qualitatively similar to those reported and shown elsewhere for other

• , resulting in 1g• and 1h• being more reducing monomers than their non-methoxylated analogues 1b• and 1e•, respectively. Cyclic voltammograms of both 1H and 12 both reveal irreversible oxidations (with the corresponding 1+ reductions seen in subsequent reductive cycles, see Figure 6 for examples). These 1H

• (located and refined for 1bH, geometrically placed for the others). Structures of the cations from the single crystal structures of 1g+I− (left), 1h+PF6− (center), and 1i+PF6− (right), shown with 50% thermal ellipsoids and excluding hydrogen atoms and counter anions. Cyclic voltammograms (50 mV s−1, THF

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• other two have imine character [11][12]. They are rigid, planar molecules which feature macrocyclic aromaticity due to the cyclic delocalisation of π electrons [13]. The well-defined macrocyclic cavity termed the coordination core, can encompass one, two, or more central ions (typically metal/metalloid

• cations), forming coordination compounds wherein the central ion acquires a square planar [14], square pyramidal [15], or an octahedral coordination environment [16]. On the opposite side, crown ethers are cyclic molecules composed of carbon and oxygen atoms forming the macrocycle. Depending on the size

• with trifluoroacetic acid (TFA) resulted in a cationic 40-H+. Cyclic voltammetry and differential pulse voltammetry were performed to investigate the electrochemical properties of 40-H+. The cation exhibited two reversible oxidations and two to three reductions. The redox potentials were influenced by

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• properties of the four CILs were probed using solution cyclic voltammetry (CV; Figure 4) and differential pulse voltammetry (DPV; Supporting Information File 1, Figures S27–S30), using dichloromethane as the solvent. For all reversible reduction or oxidation waves, HOMO and LUMO energy levels were determined

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• necessary. MF-ROMP, also termed photo-ROMP, is a novel technique to polymerize cyclic olefins. It begins with the reductive quenching of an photoexcited photocatalyst (PC) at an enol ether initiator to produce a radical cation carrier [90]. Then, the carrier undergoes cyclic addition with a cyclic olefin

• soluble upon radiation, respectively. Some early negative photoresists undergo a photochemical crosslinking process of 1,3-diene cyclic polymers [190] (cf. section 3.2), but such systems are no longer studied due to the poor resolution and sensitivity. On the other hand, positive resists based on

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• content membrane increase. Keywords: cholesterol; cyclodextrins; liposome; membrane permeability; Introduction Cyclodextrins (CDs) are a family of cyclic oligosaccharides made of glucopyranose units connected by α-1,4-glycosidic bonds. They possess a cone-shaped molecular structure with a hydrophobic

Complexes of resorcin[4]arene with secondary amines: synthesis, solvent influence on “in-out” structure, and theoretical calculations of non-covalent interactions

• Waldemar Iwanek

Beilstein J. Org. Chem. 2023, 19, 1525–1536, doi:10.3762/bjoc.19.109

• substituents with R[4]A in ethanol were synthesized. The composition of the complexes was determined based on the integration of amine proton signals in the 1H NMR spectra. For small molecule sec-amines such as N,N-dimethylamine, N,N-diethylamine, and cyclic amines (pyrrolidine, piperidine, morpholine, N

• “in” complexes. These are amines in which the size of the alkyl groups does not exceed the size of the ethyl group and cyclic sec-amines with five and six-membered rings. Pyrrolidine is the sec-amine that is most “structurally matched” to the size of the R[4]A cavity. For amines with longer alkyl

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• iminium group. In addition to assessing how the effects of the above berberine modifications could enhance the activity of B1, we also examined the influence of the rigid cyclic structure of compound B1 by preparing the non-cyclic charged variants B12 and B13 (Scheme 4). Our exploration of non-cyclic

• B13 can change its charge state depending on local environment, while the methylated derivative B12 remains a fixed-charge species. While some previous reports have pointed to the cyclic structure as essential for berberine activity, these non-cyclic variants did show some modest activity, albeit

• desired derivatives. Unexpected oxidation side-product B2, B4, and B6 were also isolated from certain reaction mixtures. Direct modification of the original berberine structure. Preparation of non-cyclic charged variants of B1. Partial reduction of compound B1 to B14. Synthesis of the substituted 2

Unraveling the role of prenyl side-chain interactions in stabilizing the secondary carbocation in the biosynthesis of variexenol B

• Moe Nakano,
• Rintaro Gemma and
• Hajime Sato

Beilstein J. Org. Chem. 2023, 19, 1503–1510, doi:10.3762/bjoc.19.107

• 180,000 terpenoid compounds have been reported to date [1][2][3][4]. One of the most intriguing point is that all diversified structures are synthesized from common starting materials, isoprenoids. Reactions that generate complex cyclic structures and multiple stereocenters from linear achiral precursors

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• first thiolation and intramolecular cyclization of propargyl azides the removal of N2 and a proton. Subsequently, monothiolated perroles were subjected to the second thiolation process to prepare 3,4-bisthiolated pyrroles. Cyclic voltammetry and DFT calculations revealed that the 3,4-bisthiolated

• formation of three-membered cyclic sulfonium ion II followed by ring-opening of sulfonium ion and intramolecular cyclization. The use of a Lewis base/Brønsted acid catalysis system for the sulfenylation of aromatic substrates 4 was reported by Gustafson et al. (Scheme 55) [87]. In the method, catalyst P

• cyclization transformation involving activation of the electrophilic sulfur reagent by PhSePh with the assistance of TMSOTf to form transition state I. Intermediate II formed through capturing of sulfonium by selenium. Then, II reacted with 136 to give regioselective cyclic thiiranium ion III. Nucleophilic

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

• Nosheen Beig,
• Varsha Goyal and
• Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

• atom(s) or another heteroatom into the vacant p-orbital (LUMO) at the carbene carbon atom (Figure 2). In fact, the donation of lone pair electrons to the carbenic center leads to an ylidic structure which induces a “push–pull” effect thereby enhancing the stability of the NHC. The cyclic structure of

• . The hydrosilylation of aryl, alkyl, and cyclic ketones could be accomplished with excellent yields (Scheme 35) [48]. In 2011, Gawley and co-worker reported an excellent reactivity and enantioselectivity of a C2-symmetric NHC–Cu(I) complex for the catalytic hydrosilylation of a variety of carbonyl

• arylaluminium reagents to five-, six-, and seven-membered β-substituted cyclic enones (Scheme 42). It is obvious that the NHC–Cu(I) complexes are generated in situ through transmetallation. For arylation reactions, Me2(Ar)Al reagents were used. The substrates having a variety of substituents (R = CH2Bn, n-Bu

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

• Feng Chen,
• Xiu-Hua Xu,
• Zeng-Hao Chen,
• Yue Chen and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2023, 19, 1372–1378, doi:10.3762/bjoc.19.98

• primary carboxylic acids but also secondary carboxylic acids (3n−s). We were pleased to find that cyclic carboxylic acids, including strained 3- and 4-membered rings, participated in this transformation and delivered the corresponding products in good yields. It should be mentioned that aromatic and more

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• acyl group. Then, the phosphocholine polar head group was introduced with a sequential one-pot procedure using first 2-chloro-2-oxo-1,3,2-dioxaphospholane (12.7) to produce a cyclic phosphate as intermediate that subsequently reacted with trimethylamine to produce thio-PAF 12.8. The opening of

• produce 15.2a [99] (Figure 15A and B) or with functionalized furane to produce 15.2b. The acylation was also achieved by reaction with cyclic acid anhydride to place in ω-position a carboxylic acid function as exemplified with 15.3a [98]. The acetyl group present in the structure of PAF in position sn-2

• 22.10. However, the last step features the lower yield (54%) of this 8-step synthesis. In 1994, Bittman et al. reported an alternative strategy to introduce the phosphocholine moiety by the preparation of a cyclic phosphite as a key intermediate [119]. This one-pot three-step sequence starts with the

Organic thermally activated delayed fluorescence material with strained benzoguanidine donor

• Alexander C. Brannan,
• Elvie F. P. Beaumont,
• Nguyen Le Phuoc,
• George F. S. Whitehead,
• Mikko Linnolahti and
• Alexander S. Romanov

Beilstein J. Org. Chem. 2023, 19, 1289–1298, doi:10.3762/bjoc.19.95

• significantly shorter (0.4 Å) than the 3.74(3) Å average distance between nearest neighbor carbazole ligands in 4CzIPN, indicative for much stronger intermolecular interactions. Cyclic voltammetry was used to analyze the redox behavior of 4BGIPN in THF solution containing [n-Bu4N]PF6 as supporting electrolyte

• recorded using a Bruker AVIII HD 500 MHz NMR spectrometer. 1H NMR spectra (500.19 MHz) and 13C{1H} (125.79 MHz) were referenced to dichloromethane-d2 at δ 5.32 (13C, δ 53.84). All electrochemical experiments were performed using an Autolab PGSTAT 302N computer-controlled potentiostat. Cyclic voltammetry

• ) possible isomers for 4BGIPN material. Ellipsoids are shown at the 50% level where hydrogen atoms are omitted for clarity. Full range cyclic voltammogram for 4BGIPN. Recorded using a glassy carbon electrode in THF solution (1.4 mM) with [n-Bu4N]PF6 as supporting electrolyte (0.13 M), scan rate 0.1 Vs−1. UV

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp³)–H to construct C–C bonds

• Hui Yu and
• Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

• ][48][49][50]: 1) CuII → CuI → CuII; 2) CuI → CuIII → CuI; 3) CuII → CuIII → CuI → CuII. In 2006, Li et al. demonstrated that the CDC reaction of the C(sp3)–H bond of malonate diesters or other active methylene compounds with the C(sp3)–H bond adjacent to the oxygen atom of cyclic and open-chain

• oxidative alkylation of cyclic benzyl ethers with malonates or ketones. Oxygen is used as a terminal oxidant at atmospheric pressure. The key intermediate of this oxidative coupling reaction is benzyl alcohol intermediate C (Scheme 4) [52]. The generation of N–O radicals from NHPI in the presence of oxygen

• triggers the whole coupling reaction. The potential application of NHIP as a catalyst for oxidative coupling reactions with oxygen as a terminal oxidant was explored. In 2011, Garcia-Mancheño et al. developed a Cu-catalyzed CDC of cyclic benzyl ethers 10 with aliphatic or α,β-unsaturated aldehydes 13 or 14

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

• Olfa Mhasni,
• Jalloul Bouajila and
• Farhat Rezgui

Beilstein J. Org. Chem. 2023, 19, 1251–1258, doi:10.3762/bjoc.19.93

• Toulouse, France University of Tunis El Manar, Laboratory of Organic Chemistry, Faculty of Sciences, Campus, 2092 Tunis, Tunisia 10.3762/bjoc.19.93 Abstract A highly α-regioselective N-nucleophilic allylic substitution of cyclic MBH alcohols and acetates with imidazole or benzimidazole, in toluene at

• , such alcohols were in situ converted into the corresponding O-allyl carbamates as leaving groups, followed by their reaction with imidazoles, affording the SN2’ products 3 (Scheme 1, reaction 1, iii). Correlatively, we have previously reported a direct amination of cyclic MBH alcohols 4 with morpholine

• that nucleophilic allylic substitution reactions of acyclic/cyclic MBH adducts 1, 4, or 5, bearing good or poor leaving groups, using imidazole derivatives as nucleophilic reagents, have not been extensively developed. Therefore, in continuation of our previous study on the nucleophilic allylic

Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction

• Ziying Xiao,
• Fengshun Xu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1234–1242, doi:10.3762/bjoc.19.91

• to explain the formation of different cyclic compounds, a plausible reaction mechanism was proposed in Scheme 2 on the basis of the present experiments and the previous works [51][52][53]. Firstly, 3-isatyl-1,4-dicarbonyl compound 1 was converted to a carbanion in the presence of base. In the

• , the nucleophilic addition of the amino anion to the carbonyl group in the of 1,3-cyclohexanedione scaffold resulted in cyclic intermediate C. Thirdly, the elimination of water from intermediate C gave the isolated product 3. In the case of the intermediate B2 with a benzoyl group, there are two kinds

• of reactive carbonyl groups in intermediate B2, one carbonyl group is in the benzoyl moiety and another carbonyl group is in the 1,3-cyclohexanedione part. In this case the amino group selectively attacked the benzoyl group to give cyclic intermediate D, while the two carbonyl groups in the 1,3

Radical ligand transfer: a general strategy for radical functionalization

• David T. Nemoto Jr,
• Kang-Jie Bian,
• Shih-Chieh Kao and
• Julian G. West

Beilstein J. Org. Chem. 2023, 19, 1225–1233, doi:10.3762/bjoc.19.90

• , including terminal aliphatic alkenes, internal (cyclic) styrenes, and one example of a nonconjugated diene, suggesting RLT to be compatible with many functionalities. The diastereoselectivity of the reaction varies, with high anti-selectivity being achieved with cyclic styrenes and low diastereoselectivity

• intermediate. RLT to this radical from another azide ligand leads to a diazidated product. The overall scope of both reports suggests that the diazidation of simple to complex drugs/natural product-derived alkene substrates is readily achievable, including highly substituted and cyclic aliphatic alkenes

Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors

• Grace A. Lowe

Beilstein J. Org. Chem. 2023, 19, 1198–1215, doi:10.3762/bjoc.19.88

• energy orbitals on photooxidized or photoexcited photosensitizers with more positive potentials. Cyclic voltammetry can be used to measure ground-state redox potentials by varying the potential at a working electrode with respect to a reference electrode and measuring the current response [19]. In

• photocatalysis. Cyclic voltammetry carried out in standard conditions for mimicking an acetonitrile system had not been close enough to the catalytic conditions to get the required redox potentials. The difference between the oxidation potential of a sacrificial donor and the reduction potential of the excited

• -workers published a study in which they used a cyclic tertiary amine sacrificial donor that they had designed to be regenerated [32]. This was significant because instead of replacing amine sacrificial donors with redox mediators, this paper proposed an alternate strategy of an ex-situ regeneration of

Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control

• Carlee A. Montgomery and
• Graham K. Murphy

Beilstein J. Org. Chem. 2023, 19, 1171–1190, doi:10.3762/bjoc.19.86

• being slightly different (0.18 e and 0.19 e) due to its non-planarity, whereas the cyclic, planar variant’s potentials were each 0.20 e [88][89]. The strength of the σ-holes for I-8 and I-9 were far greater than those of other HVI reagents, which was unsurprising given that its iodine atom was

• potentials of 0.075 e and 0.048 e. The cyclic dimedone-derived ylide I-12 showed similar potentials of 0.080 e and 0.052 e, as did the Meldrum’s acid-derived ylide I-13 (0.085 e and 0.057 e). Whether the ylide was cyclic or acyclic, the σ-hole opposite the β-dicarbonyl motif was consistently greater in

• had occurred, which was attributed to halogen bond complex formation. In 2019, the Murphy group reported the first transformation induced by blue LED irradiation of cyclic and acyclic iodonium ylides (e.g., 6) and alkenes, which generated cyclopropanes 40 in yields up to 96% (Scheme 8) [125]. UV–vis