Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

• Alexander S. Hampton,
• David R. W. Hodgson,
• Graham McDougald,
• Linhua Wang and
• Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

• of gem-dihalo groups to corresponding CF2 derivatives using silver tetrafluoroborate [5] or mercury(II) fluoride [6], deoxyfluorination of carbonyl derivatives using diethylaminosulfur trifluoride (DAST) or related Deoxo-Fluor and Xtalfluor reagents [7][8]. Alternatively, oxidative

• fluorodesulfurizations of carbonyl derivatives using a combination of sources of halonium and fluoride ions such as 1,3-dibromo-5,5-dimethylhydantoin (DBH) and tetrabutylammonium dihydrogen trifluoride have been achieved [9][10][11]. The transformation of methylene to difluoromethylene using electrophilic fluorinating

Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold

• Viktoria A. Ikonnikova,
• Cristina Cheibas,
• Oscar Gayraud,
• Alexandra E. Bosnidou,
• Nicolas Casaretto,
• Gilles Frison and
• Bastien Nay

Beilstein J. Org. Chem. 2024, 20, 162–169, doi:10.3762/bjoc.20.15

• are excellent substrates for such reactions, affording electrophilic carbonyl derivatives susceptible to react with nucleophiles in the acidic reaction mixture [4][5][6][7][8]. Consequently, the Hock rearrangement is likely to be part of tandem processes involving this carbonyl function [9][10][11

α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping

• Angel Palillero-Cisneros,
• Paola G. Gordillo-Guerra,
• Fernando García-Alvarez,
• Olivier Jackowski,
• Franck Ferreira,
• Fabrice Chemla,
• Joel L. Terán and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103

• (MgSO4), and concentrated under reduced pressure to provide the crude product which was then purified by column chromatography on silica gel. 3. Procedure for the air-promoted tandem 1,4-addition–aldol reaction between dialkylzinc reagents, α-(aminomethyl)acrylates and carbonyl derivatives (preparation

Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

• Alemayehu Gashaw Woldegiorgis and
• Xufeng Lin

Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185

• with α-methylene carbonyl derivatives 78 catalyzed by a chiral phosphoric acid. In the presence of (R)-CPA 9, the Friedländer heteroannulation reaction between aromatic amines 77 and the carbonyl derivative 78 was carried out to form imine I-21, which tautomerized to generate intermediate I-22. Under

Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure

• Agnieszka Grajewska,
• Maria Chrzanowska and
• Wiktoria Adamska

Beilstein J. Org. Chem. 2021, 17, 2511–2519, doi:10.3762/bjoc.17.168

• Petasis three-component reaction followed by the Pomeranz–Fritsch–Bobbitt cyclization. The Petasis reaction between boronic acids, carbonyl derivatives, and amines, leading to the formation of amino acids and the Pomeranz–Fritsch–Bobbitt cyclization of amino acetals, leading to the construction of C-1

Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives

• Emese Gal,
• Luiza Gaina,
• Hermina Petkes,
• Alexandra Pop,
• Castelia Cristea,
• Gabriel Barta,
• Dan Cristian Vodnar and
• Luminiţa Silaghi-Dumitrescu

Beilstein J. Org. Chem. 2020, 16, 2929–2936, doi:10.3762/bjoc.16.242

• of aldimine and ketoimine substrates under mild conditions [18]. Early studies reported a positive effect of sonication on the classical aminocyanation procedures. The reaction rate of the classical Strecker reaction using cyanide salts, amines and aromatic carbonyl derivatives [19] or piperidone [20

Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions

• Clément Q. Fontenelle,
• Thibault Thierry,
• Romain Laporte,
• Emmanuel Pfund and
• Thierry Lequeux

Beilstein J. Org. Chem. 2020, 16, 1936–1946, doi:10.3762/bjoc.16.160

• already reported in the literature from oxetane-containing α,β-unsaturated carbonyl derivatives through a Lewis acid-catalyzed rearrangement [31]. When the previous conditions (HBr/AcOH) were tried (3.5 h, 0 °C to 20 °C), hydroxymethyllactone 14 (87%, Table 4, entry 1) was the main product with traces of

Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor

• Dalel El-Marrouki,
• Sabrina Touchet,
• Abderrahmen Abdelli,
• Hédi M’Rabet,
• Mohamed Lotfi Efrit and
• Philippe C. Gros

Beilstein J. Org. Chem. 2020, 16, 1722–1731, doi:10.3762/bjoc.16.144

• ][45][46][47]. Moreover, arylhydrazones and arylhydrazines/hydrazines can be used as well, respectively, as partners in [4 + 2] cyclization reactions [48][49][50][51] or by reacting mostly with carbonyl derivatives [52][53][54][55]. From the state-of-the-art, a strategy that promotes the synthesis of

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

• -systems: heteroarenes and electron-poor alkenes in particular. Using the tools of organophotocatalysis, this reactive intermediate can be directly obtained from carbonyl derivatives, such as aldehydes, α-keto acids, oxalates, or carbamates through oxidative or reductive decarboxylations, oxidative

Recent advances in Cu-catalyzed C(sp³)–Si and C(sp³)–B bond formation

• Balaram S. Takale,
• Ruchita R. Thakore,
• Elham Etemadi-Davan and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

• difficulties typically associated with conversions of pinacol esters to trifluoroborates. An asymmetric 1,4-borylation of α,β-unsaturated carbonyl derivatives, e.g., 428 and 429, was reported using a combination of Cu(MeCN)2PF6/L47 with either bisboronic acid (BBA, 430) or tetrakis(dimethylamino)diboron (431

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

• Delphine Pichon,
• Jennifer Morvan,
• Christophe Crévisy and
• Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

• , the acylimidazole moiety constituted a privileged surrogate of esters, amides, ketones, and aldehydes. Indeed, this peculiar function, which was readily accessible from the corresponding aldehydes or Weinreb amides, could be efficiently converted into a wide range of carbonyl derivatives, as depicted

Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

• Anthony Choi,
• Rebecca M. Morley and
• Iain Coldham

Beilstein J. Org. Chem. 2019, 15, 1480–1484, doi:10.3762/bjoc.15.149

• carboxylic acid derivative, particular an ethyl ester group [55][56][57][58][59]. Here we describe a wider scope that extends the examples to alternative carbonyl derivatives and alternative alkenes, hence providing novel pyrroloquinoline compounds. Results and Discussion To test the feasibility of the

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• performing a visible light-driven oxidative cyclisation of arylamidines using Rose Bengal as the photocatalyst, in the presence of base and CBr4 as the oxidant (Scheme 25) [69]. The scope of the reaction is restricted to mono-substituted benzenes and lacks any carbonyl derivatives as ligands. The reaction

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

• Gwendal Grelier,
• Benjamin Darses and
• Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

• efficiency of the reaction is limited by the need to use 2 equivalents of allenes 20 to obtain good yields. λ3-Iodane reagents: alkynylbenziodoxolone Ethynylbenziodoxolone (EBX) is a powerful reagent to perform the electrophilic alkynylation of various functional groups such as carbonyl derivatives, thiols

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• behavior to the pyrene–adenine 5 that closely resemble the properties of unsubstituted pyrene (Table 1). These results show that the two aromatic parts – pyrene and nucleobase – of conjugates 4 and 5 are not electronically coupled. The absorption and emission properties of pyrene–carbonyl derivatives 2 and

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• carbonyl derivatives 71 [197]. It must be noted that when the organometallic complex possessed halogen–metal moiety, then Me3SiBr can induce halogen exchange [198]. The use of bromotrimethylsilane to prepare phosphonic acid from dialkyl phosphonate is rarely associated with undesired side reactions

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• hydrogenation of internal alkynes in presence of other functional groups other than alcohols was examined, for instance using the carbonyl derivatives methyl phenylpropiolate (14) and 4-phenyl-3-butyn-2-one (15). Both compounds were hydrogenated using the Pd@Monobor monolithic catalyst under mild conditions

β-Amino functionalization of cinnamic Weinreb amides in ionic liquid

• Yi-Ning Wang,
• Guo-Xiang Sun and
• Gang Qi

Beilstein J. Org. Chem. 2016, 12, 2372–2377, doi:10.3762/bjoc.12.231

• -amino carbonyl derivatives. Surprisingly, there have been only a few successful preparations for β-amino Weinreb amides to date. One of which is the addition of the enolate of commercially available N-methoxy-N-methylacetamide to sulfinimines to generate the corresponding N-sulfinyl β-amino Weinreb

Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols

• Bianca Rossi,
• Nadia Pastori,
• Simona Prosperini and
• Carlo Punta

Beilstein J. Org. Chem. 2015, 11, 66–73, doi:10.3762/bjoc.11.10

• . The new conditions prevent the undesired domino side-reaction from occurring, whereby the ketyl radical undergoes fast oxidation and generates new carbonyl derivatives, which in turn competes with ketones in the formation of imines. Titanium salts play a key role, both favoring the formation of

A convenient enantioselective decarboxylative aldol reaction to access chiral α-hydroxy esters using β-keto acids

• Zhiqiang Duan,
• Jianlin Han,
• Ping Qian,
• Zirui Zhang,
• Yi Wang and
• Yi Pan

Beilstein J. Org. Chem. 2014, 10, 969–974, doi:10.3762/bjoc.10.95

• aldehydes and carboxylic acids. Other less reactive carbonyl derivatives such as isatins [11][12], ketimines [13] and sulfonylimines [14] have also been employed with β-keto acids in the decarboxylative addition processes. α-Keto esters as surrogates of aldehydes for the generation of chiral alcohols by

Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination

• Łukasz Górecki,
• Artur Mucha and
• Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 883–889, doi:10.3762/bjoc.10.85

• skeleton and a phosphorus atom. For the C9 ketones a phosphonate–phosphate rearrangement, associated with a tandem elimination of the piperidine fragment, was evidenced. Keywords: carbonyl derivatives; dialkyl phosphite addition; organophosporus; phosphonate–phosphate rearrangement; quinine oxidation

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

• Lucio Melone and
• Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

• amount of acetaldehyde to 10% mol ratio with respect to the alkyl aromatic [58][59] (Scheme 21). Thus, while the NHPI/AQ catalytic system was particularly effective in converting alkylaromatics to the corresponding carbonyl derivatives, this approach represents a valuable alternative when hydroperoxides

Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents

• Paul Knochel,
• Matthias A. Schade,
• Sebastian Bernhardt,
• Georg Manolikakes,
• Albrecht Metzger,
• Fabian M. Piller,
• Christoph J. Rohbogner and
• Marc Mosrin

Beilstein J. Org. Chem. 2011, 7, 1261–1277, doi:10.3762/bjoc.7.147

• transition metal salts and in a very limited scope. Recently, we showed that the cheap and non-toxic main group Lewis acid MgCl2 allows smooth addition reactions of different aromatic, heteroaromatic, alkyl and benzylic zinc reagents to various carbonyl derivatives and carbon dioxide without the use of polar

Continuous gas/liquid–liquid/liquid flow synthesis of 4-fluoropyrazole derivatives by selective direct fluorination

• Jessica R. Breen,
• Graham Sandford,
• Dmitrii S. Yufit,
• Judith A. K. Howard,
• Jonathan Fray and
• Bhairavi Patel

Beilstein J. Org. Chem. 2011, 7, 1048–1054, doi:10.3762/bjoc.7.120

• manufacturing, we developed continuous flow microreactor systems that enabled gas/liquid fluorination reactions between fluorine and various substrates to occur in very efficient processes [19][20][21]. Fluoro-carbonyl derivatives can, in principle, be utilised as building blocks for the preparation of more

A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates

• Erwan Le Gall,
• Antoine Pignon and
• Thierry Martens

Beilstein J. Org. Chem. 2011, 7, 997–1002, doi:10.3762/bjoc.7.112

• trialled unsuccessfully, a different strategy based on the formation of solid bonds indicated that carbonyl derivatives such as acetyl chloride or methyl chloroformate were, in contrast, efficient activators of the C=N double bond, albeit used in stoichiometric amounts. This result is consistent with some