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

Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor

• Koichi Mitsudo,
• Atsushi Osaki,
• Haruka Inoue,
• Eisuke Sato,
• Naoki Shida,
• Mahito Atobe and
• Seiji Suga

Beilstein J. Org. Chem. 2024, 20, 1560–1571, doi:10.3762/bjoc.20.139

• cyanoarenes, nitroarenes, quinolines, and pyridines using a proton-exchange membrane (PEM) reactor was developed. Cyanoarenes were then reduced to the corresponding benzylamines at room temperature in the presence of ethyl phosphate. The reduction of nitroarenes proceeded at room temperature, and a variety of

• cyanoarenes is a straightforward and powerful method for the synthesis of primary amines [5], and the reduction of nitroarenes is useful for the synthesis of aniline derivatives [6][7][8][9][10][11]. Nitrogen-containing aliphatic heterocycles, such as piperidines and tetrahydroquinolines, are key motifs in

• ]. As mentioned above, there have been several reports on reductive reactions using PEM reactors; however, the application of PEM reactors for precise chemical transformations remains limited. To the best of our knowledge, no reports are available on the efficient reduction of cyanoarenes, quinolines

Mechanistic investigations of polyaza[7]helicene in photoredox and energy transfer catalysis

• Johannes Rocker,
• Till J. B. Zähringer,
• Matthias Schmitz,
• Till Opatz and
• Christoph Kerzig

Beilstein J. Org. Chem. 2024, 20, 1236–1245, doi:10.3762/bjoc.20.106

• ][13][14][15]. Most of the established organic catalysts (acridinium salts [16][17][18][19], cyanoarenes [8][20][21][22], quinones [23][24], etc.) [10][25] are cationic or electron-deficient and tend to act as excited state oxidants in a reductive quenching cycle. Only recently, more reducing catalyst

• classes have been investigated, including second-generation cyanoarenes [8], arylamines [26], phenothiazines, phenazines and phenoxazines [9][27][28], which can act as excited state reductants comparable to precious metal-based photoredox catalysts. Singlet-excited organic chromophores often have short

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

• Lucas Guillemard and
• Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

• ) [38][39], and more recently, organic compounds (cyanoarenes, xanthenes, thiazines, pyryliums or acridiniums) [40], emerged. These molecules capable of harvesting visible light from simple household bulbs or easily accessible LEDs, opened the door towards the design of numerous electron or energy

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

• Stephanie G. E. Amos,
• Marion Garreau,
• Luca Buzzetti and
• Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

• , such as acridiniums (OD1–4), cyanoarenes (OD5–8), diaryl ketones (OD9/10), flavins (OD11/12), xanthenes (OD13–15), thiazines (OD16/17) and various other dyes, such as OD18–21, have been exploited (Figure 1), and the field of organic photocatalysis has been extensively covered by various reviews [16][19

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• Classically, benzonitrile was synthesized via Sandmeyer reaction, Rh/Co catalytic systems, or electrophilic reactions, and such reactions suffered from poor site selectivity. Therefore, utilizing the versatility of cyanoarenes, recently, Nicewicz and his team reported the preparation of cyanated products

One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling

• Roman Yu. Peshkov,
• Elena V. Panteleeva,
• Wang Chunyan,
• Evgeny V. Tretyakov and
• Vitalij D. Shteingarts

Beilstein J. Org. Chem. 2016, 12, 1577–1584, doi:10.3762/bjoc.12.153

• -coupling; cyanoarenes; reactive intermediates; reductive alkylation; Introduction Alkylcyanobiphenyls are well known largely due to their mesogenic properties, which were discovered by Gray in the 1970th [1][2]. Alkylcyanobiphenyls and their analogs (e.g., dialkyl and alkoxy alkyl derivatives) are still

• approach based on anionic forms of cyanoarenes as effective cross-coupling reagents toward neutral unactivated substrates [26][27], but also expand the knowledge about nucleophilic mechanisms such as aromatic substitution of a hydrogen atom (SNH) [28] and the vicarious substitution [29]. Results and

• with ω-substituted-alkyl bromides 6a–f. Interaction of dianion 12– with cyanoarenes 2b–i, followed by alkylation of intermediate anions 3b–i with butyl bromide 6a. Supporting Information Supporting Information File 550: Experimental section and 1H, 13C and 19F NMR spectra of all synthesized compounds

Simple synthesis of pyrrolo[3,2-e]indole-1-carbonitriles

• Adam Trawczyński,
• Robert Bujok,
• Zbigniew Wróbel and
• Krzysztof Wojciechowski

Beilstein J. Org. Chem. 2013, 9, 934–941, doi:10.3762/bjoc.9.107

• °C) led to a mixture of the expected product 9a and the product 10a in that the cyano group was reduced to a methyl substituent (Scheme 4). There is a literature precedence [19] for similar transformations of cyanoarenes into corresponding methyl derivatives upon transfer hydrogenation with ammonium