Electrochemical synthesis of cyclic biaryl λ³-bromanes from 2,2’-dibromobiphenyls

• Andrejs Savkins and
• Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

• notable examples underscore the remarkable potential of cyclic diaryl λ3-bromanes in the development of efficient synthetic transformations. Cyclic diaryl λ3-bromanes 1 are typically synthesized using a method developed by Sandin and Hay in 1952 [11] that relies on the excellent nucleofugality of

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

• Dmitry E. Shybanov,
• Maxim E. Kukushkin,
• Eugene V. Babaev,
• Nikolai V. Zyk and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

• adducts of formaldehyde condensation are formed under milder conditions and are highly reactive, which is important for further synthetic transformations. However, due to the high carbonyl reactivity of formaldehyde, its interaction with active methylene compounds is often complicated by polycondensation

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

• Seungmin Lee,
• Minsuk Kim,
• Hyewon Han and
• Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

• advancements in the synthetic transformations of dioxazolones, with particular examples of copper salts. Keywords: amidation; copper salts; dioxazolones; electrophilic nitrogen; N-acyl nitrene; Introduction Dioxazolones, first synthesized and reported by Beck and co-workers [1], have been employed as

Recent advances in electrochemical copper catalysis for modern organic synthesis

• Yemin Kim and
• Won Jun Jang

Beilstein J. Org. Chem. 2025, 21, 155–178, doi:10.3762/bjoc.21.9

• catalytic systems (merging electrochemistry with transition-metal catalysis) has led to the development of new, efficient, and chemo- and stereoselective synthetic transformations. This review highlighted the recent developments in dual catalytic reactions involving copper and electrocatalysis, including C

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

• hydrazones can act as radical acceptors for the synthesis of functionalized amines or hydrazones through reductive functionalization [21][25][26] or oxidative C(sp2)–H functionalization [27][28], respectively. Consequently, given their rich reactivity profile, exploring new synthetic transformations of

Syntheses and medicinal chemistry of spiro heterocyclic steroids

• Laura L. Romero-Hernández,
• Ana Isabel Ahuja-Casarín,
• Penélope Merino-Montiel,
• Sara Montiel-Smith,
• José Luis Vega-Báez and
• Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

• the future design of more potent and selective drugs. Keywords: biological activity; drug development; heterocycle; spiro steroid; synthetic transformations; Introduction Small-ring heterocycles constitute valuable scaffolds in medicinal chemistry for generating biologically active derivatives

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

• Mithu Roy,
• Bitan Sardar,
• Itu Mallick and
• Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

• is highly expected that many groups will explore many new useful synthetic transformations based on renewable feedstocks, such as alcohols and acids, which will likely lead to even more exciting opportunities in the near future. Generation of alkyl and acyl radicals via C–O bond breaking. General

Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines

• Geng-Xin Liu,
• Xiao-Ting Jie,
• Ge-Jun Niu,
• Li-Sheng Yang,
• Xing-Lin Li,
• Jian Luo and
• Wen-Hao Hu

Beilstein J. Org. Chem. 2024, 20, 661–671, doi:10.3762/bjoc.20.59

• amines. Scale-up reactions and synthetic transformations. Reaction conditions: a) LiAlH4, THF, 0 °C; b) MeMgBr, THF, rt to reflux; c) NaOH, MeOH, 60 °C, d) EDCI, DMAP, BnNH2, DCM, rt; e) EDCI, DMAP, Et3N, HN(OMe)(Me)·HCl, DCM, rt; f) MeMgBr, THF, 0 °C to rt; g) Pd/C, HCO2NH4, 65 °C. For more details, see

Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet–Spengler reaction

• Elena Y. Mendogralo and
• Maxim G. Uchuskin

Beilstein J. Org. Chem. 2023, 19, 991–997, doi:10.3762/bjoc.19.74

• of some of the products was investigated and selected synthetic transformations of the obtained tetrahydrofuro[3,2-c]pyridines were shown. Keywords: acid hydrolysis; 1,4-diketone; tetrahydrofuro[3,2-c]pyridines; Paal–Knorr reaction; Pictet–Spengler reaction; Introduction Hydrogenated furo[3,2-c

Asymmetric tandem conjugate addition and reaction with carbocations on acylimidazole Michael acceptors

• Brigita Mudráková,
• Renata Marcia de Figueiredo,
• Jean-Marc Campagne and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 881–888, doi:10.3762/bjoc.19.65

• ]. These non-traditional electrophiles allow access to structurally highly interesting motifs. In addition, they are amenable to valuable synthetic transformations such as oxidative ring contraction of the cycloheptatrienyl ring or reduction of the benzodithiolyl group. In this context, we decided to study

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

• Péter Kisszékelyi and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

• organic synthetic transformations. Chiral metal enolates obtained by asymmetric conjugate additions of organometallic reagents are structurally complex intermediates that can be employed in many transformations. In this review, we describe this burgeoning field that is reaching maturity after more than 25

• array of organic synthetic transformations. Enolates are usually formed by deprotonation of the corresponding organic compound. However, other synthetic approaches for their generation exist, such as cleavage of enol ethers and esters, halogen–metal exchange, transmetalations, and conjugate additions to

Germacrene B – a central intermediate in sesquiterpene biosynthesis

• Houchao Xu and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

• from cations L1–L4. A) Mechanisms of formation for compounds 54, 56, 59 and 60, B) dehydration of 61 to 56, C) oxidation of 56 to 62, D) dehydration of 63 to 60 and 64 (no yields were given in the original reports for the synthetic transformations shown in this Scheme).

Microelectrode arrays, electrosynthesis, and the optimization of signaling on an inert, stable surface

• Kendra Drayton-White,
• Siyue Liu,
• Yu-Chia Chang,
• Sakashi Uppal and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2022, 18, 1488–1498, doi:10.3762/bjoc.18.156

• can be used to help prevent non-specific binding and minimize biofouling possibilities [18]. While the use of a diblock copolymer coating offers the desired stability advantage, it also rules out the use of both direct methods for conducting synthetic transformations on the array and the direct

DDQ in mechanochemical C–N coupling reactions

• Shyamal Kanti Bera,
• Rosalin Bhanja and
• Prasenjit Mal

Beilstein J. Org. Chem. 2022, 18, 639–646, doi:10.3762/bjoc.18.64

• mechanochemistry [5][6] mainly focuses on conducting synthetic transformations in solid-state or solvent-free conditions. Mechanochemistry is one of the emerging avenues in chemistry that can make the world more sustainable by following the “Twelve Principles of Green Chemistry” [2]. Mechanochemistry is one of the

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

• Ranadeep Talukdar

Beilstein J. Org. Chem. 2021, 17, 2102–2122, doi:10.3762/bjoc.17.137

• -mediated coupling of N-silylated 6-hydroxyindole 174 with the corresponding boronic acid 173 (Scheme 24) [114]. For further synthetic transformations of 175, N-protection with bromo esters 176 followed by hydrolysis towards acids 177a and 177b were performed. The products 177a and 177b are potent anti-HIV

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• excluded. This late-stage process by Mn catalysis, electrochemistry, and visible-light catalysis exhibits high value as a sustainable tool to investigate problematic synthetic transformations. Recently, the Ackermann group disclosed a convenient manganese-catalyzed late-stage C–H azidation of bioactive

Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: synthesis of diverse nitrogenous heterocyclic compounds

• Guanglong Pan,
• Qian Yang,
• Wentao Wang,
• Yurong Tang and
• Yunfei Cai

Beilstein J. Org. Chem. 2021, 17, 1171–1180, doi:10.3762/bjoc.17.89

• ]. In the last few years, carbon nitride-based heterogeneous photocatalysts have also been utilized for several other radical-initiated synthetic transformations [44][45][46][47][48][49][50][51][52][53][54][55][56]. However, to the best of our knowledge, the application of a CN-based photocatalyst for

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

Nitroalkene reduction in deep eutectic solvents promoted by BH₃NH₃

• Chiara Faverio,
• Monica Fiorenza Boselli,
• Patricia Camarero Gonzalez,
• Alessandra Puglisi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2021, 17, 1041–1047, doi:10.3762/bjoc.17.83

• relatively inexpensive, useful reduction reagent for developing new green synthetic transformations [6][7][8][9][10][11][12]. Compared to other bioinspired reagents, such as Hantzsch esters, AB represents a more convenient reagent that generates much less waste [10]. We have recently reported the use of

A new and efficient methodology for olefin epoxidation catalyzed by supported cobalt nanoparticles

• Lucía Rossi-Fernández,
• Viviana Dorn and
• Gabriel Radivoy

Beilstein J. Org. Chem. 2021, 17, 519–526, doi:10.3762/bjoc.17.46

• materials and it could be recovered and reused maintaining its unaltered high activity. Keywords: alkenes; cobalt nanoparticles; epoxides; oxidation; TBHP; Introduction Olefin oxidation reactions are key synthetic transformations in the production of oxygenated chemicals of high interest for both academic

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

• Anthony J. Fernandes,
• Armen Panossian,
• Bastien Michelet,
• Agnès Martin-Mingot,
• Frédéric R. Leroux and
• Sébastien Thibaudeau

Beilstein J. Org. Chem. 2021, 17, 343–378, doi:10.3762/bjoc.17.32

• -withdrawing groups – are, however, still predestined to be transient species and sometimes considered as exotic ones. Among them, the CF3-substituted carbocations, frequently suggested to be involved in synthetic transformations but rarely considered as affordable intermediates for synthetic purposes, have

• long been investigated. This review highlights recent and past reports focusing on their study and potential in modern synthetic transformations. Keywords: carbocation; organic synthesis; superelectrophile; trifluoromethyl; Introduction Carbocations are pivotal intermediates in organic chemistry, and

Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

• Michał M. Więcław and
• Bartłomiej Furman

Beilstein J. Org. Chem. 2021, 17, 115–123, doi:10.3762/bjoc.17.12

• widely used as organocatalysts. Such moieties are employed in a number of important synthetic transformations, including the aldol reaction [30], Michael addition [31], Mannich reaction [32], and hydrogenation [33]. We plan to test these possibilities in the near future. Stereochemistry and configuration

Easy access to a carbohydrate-based template for stimuli-responsive surfactants

• Thomas Holmstrøm,
• Daniel Raydan and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2020, 16, 2788–2794, doi:10.3762/bjoc.16.229

• -consuming synthetic transformations employing costly reagents [15][16][17][18]. In this paper we describe the synthesis of a new carbohydrate-based building block that can be used for the synthesis of stimuli-responsive surfactants as it has the ability to be functionalized with both metal-chelating groups

Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts

• Soundararajan Karthikeyan,
• Radha Krishnan Shobana,
• Kamarajapurathu Raju Subimol,
• J. Helen Ratna Monica and
• Ayyanoth Karthik Krishna Kumar

Beilstein J. Org. Chem. 2020, 16, 1579–1587, doi:10.3762/bjoc.16.130

• -lactams [6], quinolin-5-ones [7], spirobisglutarimides [8], indolizines [9], and spiro carbocyclic frameworks [10]. However, most of the reported synthetic transformations utilize either allylic hydroxy-protected or allyl halide-substituted MBH adducts [11][12][13][14][15][16][17][18][19][20][21][22][23

• ]. Among the known synthetic transformations using functionalized MBH adducts, cycloaddition reactions are challenging and attractive for synthetic organic chemists. In this context, acetate-functionalized Morita–Baylis–Hillman adducts have been extensively utilized over other precursors. For example

• developing a one-pot synthetic strategy will be worthwhile for pharmacologically important triazoles, such as isavuconazole, tazobactam, and ravuconazole [35]. Results and Discussion Initially, phosphonium salts were barely utilised or exploited in synthetic transformations. Later, in 2014, several organic

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125