Synthesis of fluoro-functionalized diaryl-λ³-iodonium salts and their cytotoxicity against human lymphoma U937 cells

• Prajwalita Das,
• Etsuko Tokunaga,
• Hidehiko Akiyama,
• Hiroki Doi,
• Norimichi Saito and
• Norio Shibata

Beilstein J. Org. Chem. 2018, 14, 364–372, doi:10.3762/bjoc.14.24

• . These results led us to synthesize more compounds, previously unknown sterically demanding diaryliodonium salts having a pentafluorosulfanyl (SF5) functional group at the ortho-position, that is, unsymmetrical ortho-SF5 phenylaryl-λ3-iodonium salts. Newly synthesized mesityl(2-(pentafluoro-λ6-sulfanyl

• )phenyl)iodonium exhibited the greatest potency in vitro against U937 cells. Evaluation of the cytotoxicity of selected phenylaryl-λ3-iodonium salts against AGLCL (a normal human B cell line) was also examined. Keywords: biological activity; diaryliodonium salt; fluorine; hypervalent iodine; lymphoma

• -functionalized diaryliodonium salts. These findings led us to synthesize four more previously unknown diaryliodonium salts having a sterically demanding pentafluorosulfanyl (SF5) functional group at the ortho-position, that is, unsymmetrical ortho-SF5 phenylaryl-λ3-iodonium salts. Finally, one of the new

Diels–Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

• Huangguan Chen,
• Jianwei Han and
• Limin Wang

Beilstein J. Org. Chem. 2018, 14, 354–363, doi:10.3762/bjoc.14.23

• reaction time did not improve the yield of 3aa (Table 1, entries 18–21). With the optimal reaction conditions in hand, various aryl(mesityl)iodonium salts 2 were examined. As shown in Table 2, an extensive range of substituted aryl(mesityl)iodonium salts, bearing a wide variety of substituent groups, could

• react with 1a to afford the corresponding cycloaddition adducts 3. It was observed that the reaction gave the desired products 3ab and 3ac in moderate yields of 63% and 57% when iodonium salts 2 have electron-donating groups in the para-position of the aryl moiety, such as methyl groups and tert-butyl

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

Metal and metal-free photocatalysts: mechanistic approach and application as photoinitiators of photopolymerization

• Jacques Lalevée,
• Sofia Telitel,
• Pu Xiao,
• Marc Lepeltier,
• Frédéric Dumur,
• Fabrice Morlet-Savary,
• Didier Gigmes and
• Jean-Pierre Fouassier

Beilstein J. Org. Chem. 2014, 10, 863–876, doi:10.3762/bjoc.10.83

• radical Ph• is formed (Scheme 3). Unfortunately, the oxidation reaction of Ph• by PIC•+ is rather hard [45][46][47][48][49][50][51][52] and such a system does not work. Sulfonium salts were also used as eA but the reactivity is lower than that for iodonium salts (see below) [56]. A typical efficient

Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts

• Stefan Riedmüller and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2013, 9, 1202–1209, doi:10.3762/bjoc.9.136

• The direct synthesis of N-arylated carbazoles through a palladium-catalyzed amination of cyclic iodonium salts with anilines is described. In particular, electron-poor aniline derivatives reacted smoothly with only 5 mol % of Pd(OAc)2 as catalyst to give the desired products in up to 71% yield

• . Furthermore, the reactivity of cyclic iodonium salts is compared with the reactivity of the corresponding cyclic bromonium analogues. Keywords: amination; carbazoles; hypervalent; iodine; iodonium salts; Introduction Carbazoles play an important role as core structural elements in natural products (e.g

• ] or the direct arylation [14][15] of the free NH-functionality of carbazole (path B). In the past decade, hypervalent iodine chemistry has undergone a renaissance and has developed to become a powerful area in synthetic organic chemistry. Open-chained iodonium salts are well explored in transition

A practical microreactor for electrochemistry in flow

• Kevin Watts,
• William Gattrell and
• Thomas Wirth

Beilstein J. Org. Chem. 2011, 7, 1108–1114, doi:10.3762/bjoc.7.127

• syntheses as mild, non-toxic and highly selective reagents. Iodine(III) reagents with two carbon ligands are known as iodonium salts. These salts are attractive alternatives to oxidants and catalysts based on heavy metals, as they have similar properties to those of heavy metal complexes and can, therefore

• , be used in similar reaction pathways, and are beneficial for organic synthesis due to their low toxicity and cost [20]. Iodonium salts are currently being used in three main types of reactions, namely ligand exchange, reductive elimination and ligand coupling. This is due to their highly electron

• . A general procedure for the synthesis of both, symmetric and asymmetric iodonium salts, was developed, as shown in Scheme 4, and yields of up to 72% were obtained. Initially, the conditions of the reaction were optimized with iodotoluene 8a (R1 = 4-Me) and toluene (9a) (R2 = Me). A current of 30 mA

Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds

• Carolin Fischer and
• Burkhard Koenig

Beilstein J. Org. Chem. 2011, 7, 59–74, doi:10.3762/bjoc.7.10

• resulted in good yields [4][26]. Copper-diamine-catalysed N-arylation facilitated the arylation of pyrroles, pyrazoles, indazoles, imidazoles, triazoles, benzimidazoles and indoles [27][28][29]. Besides aryl halides as the aryl donor, arylsiloxanes [30], arylstannanes [31], iodonium salts [32], aryl lead

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

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• , enamines, and thiolate anions with these reagents, albeit in low to moderate yields [28]. Neutral hypervalent iodine(III)–CF3 reagent Initial attempts by Yagupolskii and Umemoto to synthesize iodonium salts with a trifluoromethyl group were unsuccessful. Whilst iodonium salts including p