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Search for "carbonyl compounds" in Full Text gives 249 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Copper-promoted/copper-catalyzed trifluoromethylselenolation reactions

  • Clément Ghiazza and
  • Anis Tlili

Beilstein J. Org. Chem. 2020, 16, 305–316, doi:10.3762/bjoc.16.30

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  • same group studied the direct trifluoromethylselenolation of α-brominated unsaturated carbonyl compounds with [(bpy)CuSeCF3]2 and CsF as the base (Scheme 5, top) [21]. The products were obtained with good yields as a mixture of E/Z isomers. The authors postulated the formation of a copper(III) complex
  • ) bromide. The same group also reported the trifluoromethylselenolation of β-brominated unsaturated carbonyl compounds under base-free conditions (Scheme 5, bottom) [22]. Good to excellent yields were obtained for the products. The authors demonstrated that no major alterations were observed in the presence
  • carbonyl compounds with [(bpy)CuSeCF3]2 by the group of Weng. Trifluoromethylselenolation of α,β-unsaturated ketones with [(bpy)CuSeCF3]2 by the group of Weng. Trifluoromethylselenolation of acid chlorides with [(bpy)CuSeCF3]2 by the group of Weng. Synthesis of 2-trifluoromethylselenylated benzofused
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Published 03 Mar 2020

Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5-a]pyrimidines

  • Yana I. Sakhno,
  • Maryna V. Murlykina,
  • Oleksandr I. Zbruyev,
  • Anton V. Kozyryev,
  • Svetlana V. Shishkina,
  • Dmytro Sysoiev,
  • Vladimir I. Musatov,
  • Sergey M. Desenko and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2020, 16, 281–289, doi:10.3762/bjoc.16.27

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  • approaches were described for the synthesis of 7-hydroxytetrahydroazolopyrimidines by the reaction of aminoazoles, aromatic aldehydes, and some carbonyl compounds (Scheme 1, IV and Scheme 2, VI and VIII) [4][5][16][17][18][19][20][21][22][23]. Oxygen-bridged tetrahydroazolopyrimidines III were also obtained
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Published 27 Feb 2020

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

  • Jucleiton J. R. Freitas,
  • Queila P. S. B. Freitas,
  • Silvia R. C. P. Andrade,
  • Juliano C. R. Freitas,
  • Roberta A. Oliveira and
  • Paulo H. Menezes

Beilstein J. Org. Chem. 2020, 16, 168–174, doi:10.3762/bjoc.16.19

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  • ; synthesis; Introduction The propargylation of carbonyl compounds is widely used in the synthesis of biologically active natural products [1]. Some examples can be found in the synthesis of histrionicotoxin [2], rhizopodin [3], bafilomycin [4], bryostatin [5], vancosamine [6] and macrolactin A [7]. Although
  • there are several stereoselective methods described for the reaction of propargyl or allenyl organometallics with carbonyl compounds [8][9][10][11][12][13][14], the control of the regioselectivity is still a major concern. This is mainly due to the metallotropic rearrangement of propargyl and allenyl
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Published 04 Feb 2020

Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst

  • Abhijit Paul,
  • Debnath Chatterjee,
  • Srirupa Banerjee and
  • Somnath Yadav

Beilstein J. Org. Chem. 2020, 16, 140–148, doi:10.3762/bjoc.16.16

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  • following three categories: (i) by Wittig or Doebner reaction of indoles bearing a 3-aldehyde group; (ii) by 1,4- or 1,2-addition of α,β-enones or carbonyl compounds, followed by oxidation or elimination, respectively; (iii) by Pd-catalysed oxidative coupling of indoles with activated alkenes. Several
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Published 29 Jan 2020

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

  • Munmun Ghosh,
  • Valmik S. Shinde and
  • Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

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  • ) [23]. In the second report, the same electrode was applied for the asymmetric reduction of prochiral carbonyl compounds 10a and 12a, oximes 14 and gem-dibromo compounds 16 (Scheme 4). Among all of these the highest optical yield (16.6%) was obtained in the reduction of gem-dibromide substrates 16 to
  • method for the enantioselective synthesis of 4,5,5-trisubstituted γ-butyrolactones 193 using an electroreductive coupling of diaryl ketones 191 with α,β-unsaturated carbonyl compounds 190 bearing chiral auxiliaries derived from imidazolidin-2-one and oxazolidine-2-ones (Scheme 60). Compound 191 underwent
  • modified graphite cathode. Asymmetric hydrogenation of ketones using Raney nickel powder electrodes modified with optically active tartaric acid. Asymmetric reduction of prochiral activated olefins with a poly-ʟ-valine-coated graphite cathode. Asymmetric reduction of prochiral carbonyl compounds, oximes
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Published 13 Nov 2019

Unexpected one-pot formation of the 1H-6a,8a-epiminotricyclopenta[a,c,e][8]annulene system from cyclopentanone, ammonia and dimethyl fumarate. Synthesis of highly strained polycyclic nitroxide and EPR study

  • Sergey A. Dobrynin,
  • Igor A. Kirilyuk,
  • Yuri V. Gatilov,
  • Andrey A. Kuzhelev,
  • Olesya A. Krumkacheva,
  • Matvey V. Fedin,
  • Michael K. Bowman and
  • Elena G. Bagryanskaya

Beilstein J. Org. Chem. 2019, 15, 2664–2670, doi:10.3762/bjoc.15.259

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  • carbonyl compounds for the synthesis of heterocyclic compounds has been repeatedly demonstrated [2][3]. We recently used a domino reaction of amino acid, ketone and dimethyl fumarate for the one-pot synthesis of a substituted pyrrolidine, which then was converted into a reduction-resistant pyrrolidine
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Published 07 Nov 2019

1,5-Phosphonium betaines from N-triflylpropiolamides, triphenylphosphane, and active methylene compounds

  • Vito A. Fiore,
  • Chiara Freisler and
  • Gerhard Maas

Beilstein J. Org. Chem. 2019, 15, 2603–2611, doi:10.3762/bjoc.15.253

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  • -catalyzed reactions of acetylenic ketones and esters with pinacolborane have been discussed [7][8]. The Michael addition of PPh3 at acetylenic carbonyl compounds generates phosphonium/vinyl anion intermediates which have been trapped with CH-, NH-, OH- and SH-acids [5]. In this manner, the 1:1:1 reaction of
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Published 01 Nov 2019

α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

  • Shital K. Chattopadhyay,
  • Subhankar Ghosh,
  • Sarita Sarkar and
  • Kakali Bhadra

Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245

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  • reaction in the presence of Hoveyda-Grubbs 2nd generation catalyst (HG-II, 9b, 2 mol %) in refluxing DCM was found to be much faster and better yielding (77%). The product 10a was obtained as a single geometric isomer identified as E. It may be mentioned that CM with other unsaturated carbonyl compounds
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Published 24 Oct 2019

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

  • Irina G. Tkachenko,
  • Sergey A. Komykhov,
  • Vladimir I. Musatov,
  • Svitlana V. Shishkina,
  • Viktoriya V. Dyakonenko,
  • Vladimir N. Shvets,
  • Mikhail V. Diachkov,
  • Valentyn A. Chebanov and
  • Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

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  • starting material and subsequent dihydropyrimidine ring formation. The first approach [6][7] represents a two-component cyclocondensation of 5-aminotetrazole (1) as binucleophilic component and bielectrophilic α,β-unsaturated carbonyl compounds 2 (Scheme 1, reaction 1). The second method [8][9][10][11][12
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Published 08 Oct 2019

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

Graphical Abstract
  • nucleophilic fluoride source was reported by Doyle and co-worker (Scheme 5) [39]. Herein, the authors utilized a Pd/Cr cocatalytic system to generate the allylic fluorides with high regioselectivity (branched > linear). Alkyl fluorination of acidic carbonyl compounds and other compounds: In 2012, the group of
  • achieved using Et3N·3HF as the fluorine source with a high catalyst loading (20–30 mol %) affording the products in 45–92% yield [70]. The heteroatom-containing functional group (R1) is necessary for good reactivity and regioselectivity. α-Fluorination of acidic carbonyl compounds: In 2011, Shibatomi and
  • stereocontrolled acrylic allylic fluorides. Fluorination of acidic carbonyl compounds: In 2010, Itoh and co-workers [96] demonstrated the asymmetric fluorination of cyclic and acyclic β-ketoesters by using a catalytic amount of Co(acac)2 with (R,R)-Jacobsen’s salen ligand (Scheme 48). The α-fluorinated products
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Published 23 Sep 2019

α-Photooxygenation of chiral aldehydes with singlet oxygen

  • Dominika J. Walaszek,
  • Magdalena Jawiczuk,
  • Jakub Durka,
  • Olga Drapała and
  • Dorota Gryko

Beilstein J. Org. Chem. 2019, 15, 2076–2084, doi:10.3762/bjoc.15.205

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  • dichroism (ECD) and TD-DFT methods. Keywords: 1,2-diols; ECD; enamines; organocatalysis; porphyrins; silyl ethers of diarylprolinols; singlet oxygen; Introduction Carbonyl compounds are one of the most important building blocks in organic synthesis. As a consequence, there is a constant need for new
  • ) or a chiral auxiliary (i.e., oxazolidinone) into the substrate structure is required for highly stereoselective reactions [20][21][22]. ‘One-pot’ photochemical α,β-functionalization of cinnamaldehyde Over the last few years, photochemical methods for asymmetric functionalisation of carbonyl compounds
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Published 30 Aug 2019

Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition

  • Yulia V. Khoroshunova,
  • Denis A. Morozov,
  • Andrey I. Taratayko,
  • Polina D. Gladkikh,
  • Yuri I. Glazachev and
  • Igor A. Kirilyuk

Beilstein J. Org. Chem. 2019, 15, 2036–2042, doi:10.3762/bjoc.15.200

Graphical Abstract
  • compound showed a strong absorption band at 1725 cm−1 typical for carbonyl compounds and no absorption in the region 3100–3500 cm−1, suggesting that the hydroxymethyl group was affected in the reaction. The mass spectrum featured the molecular ion [M+] = 196.1335 corresponding to the molecular formula
  • C11H18NO2, which matches element analysis data. These results allowed us to assign the structure 15 to this nitroxide. Indeed, oxidation of amines with peracids is known to proceed via oxoammonium cation formation [17][18], and the latter can oxidize alcohols to carbonyl compounds [19]. The close proximity
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Published 27 Aug 2019

Metal-free mechanochemical oxidations in Ertalyte® jars

  • Andrea Porcheddu,
  • Francesco Delogu,
  • Lidia De Luca,
  • Claudia Fattuoni and
  • Evelina Colacino

Beilstein J. Org. Chem. 2019, 15, 1786–1794, doi:10.3762/bjoc.15.172

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  • a mechanochemical process. Keywords: AZADO; Ertalyte®; green chemistry; mechanochemistry; NaOCl·5H2O; selective oxidation; TEMPO; Introduction The conversion of primary and secondary alcohols to the corresponding carbonyl compounds (aldehydes and ketones, respectively) is of such importance in
  • to industrial settings. The proposed mechanism for the TEMPO-based oxidative conversion of primary and secondary alcohols to the corresponding carbonyl compounds is described in Scheme 7 and shares similarities with that postulated in other previous studies in solution. In general, NaOCl works as a
  • the atom efficiency [4][5]. The discovery of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl, commonly known as TEMPO by Lebedev and Kazarnowskii in 1960 has been hailed as a significant breakthrough in the field of redox reactions, allowing the fast and selective oxidation of alcohols to the related carbonyl
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Published 25 Jul 2019

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

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Published 19 Jul 2019

Enantioselective Diels–Alder reaction of anthracene by chiral tritylium catalysis

  • Qichao Zhang,
  • Jian Lv and
  • Sanzhong Luo

Beilstein J. Org. Chem. 2019, 15, 1304–1312, doi:10.3762/bjoc.15.129

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  • , could promote the Diels–Alder reaction with anthracenes and various unsaturated carbonyl compounds under mild conditions [13]. The use of latent carbocation catalysis with TP was examined in order to achieve enantioselective control. To our delight, TP catalyzed the asymmetric reaction affording
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Published 14 Jun 2019

Mechanochemical amorphization of chitin: impact of apparatus material on performance and contamination

  • Thomas Di Nardo and
  • Audrey Moores

Beilstein J. Org. Chem. 2019, 15, 1217–1225, doi:10.3762/bjoc.15.119

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  • stainless steel ones, since the latter caused the reactive mixture to adhere to the jars, which was not the case of the former. In another example, for the metal-free transfer hydrogenation of carbonyl compounds, PTFE was used instead of steel to eliminate the possibility of catalysis from the milling media
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Published 05 Jun 2019

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

  • Victoria V. Lipson,
  • Tetiana L. Pavlovska,
  • Nataliya V. Svetlichnaya,
  • Anna A. Poryvai,
  • Nikolay Yu. Gorobets,
  • Erik V. Van der Eycken,
  • Irina S. Konovalova,
  • Svetlana V. Shiskina,
  • Alexander V. Borisov,
  • Vladimir I. Musatov and
  • Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

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  • -bielectrophiles or their synthetic precursors in the case of three-component reactions between these amines, carbonyl compounds and CH acids. Previously, an unusual direction of the three-component reaction between 2-aminoimidazoles, aldehydes and 5,5-dimethyl-1,3-cyclohexanedione has led to the formation of the
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Published 06 May 2019

Catalytic asymmetric oxo-Diels–Alder reactions with chiral atropisomeric biphenyl diols

  • Chi-Tung Yeung,
  • Wesley Ting Kwok Chan,
  • Wai-Sum Lo,
  • Ga-Lai Law and
  • Wing-Tak Wong

Beilstein J. Org. Chem. 2019, 15, 955–962, doi:10.3762/bjoc.15.92

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  • alkene); it is called a hetero-Diels–Alder (HDA) reaction when one or more heteroatoms (most often oxygen or nitrogen) are present among the reactants, such as the use of carbonyl compounds or imines as dienophiles [1][2][3][4][5]. An asymmetric HDA reaction is capable of introducing up to four
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Published 18 Apr 2019

The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives

  • Tilman Lechel,
  • Roopender Kumar,
  • Mrinal K. Bera,
  • Reinhold Zimmer and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2019, 15, 655–678, doi:10.3762/bjoc.15.61

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  • obtained β-ketoenamides are alkenes with a remarkable assembly of functional groups: they are enamides, enol ethers and α,β-unsaturated carbonyl compounds at the same time. In addition, their methyl ketone subunit is required for some of the subsequent transformations, e.g., the synthesis of pyridin-4-ols
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Published 13 Mar 2019

Asymmetric synthesis of a high added value chiral amine using immobilized ω-transaminases

  • Antonella Petri,
  • Valeria Colonna and
  • Oreste Piccolo

Beilstein J. Org. Chem. 2019, 15, 60–66, doi:10.3762/bjoc.15.6

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  • carbonyl compounds. In a kinetic resolution, a maximum yield of 50% of the product can be obtained. Moreover, high quantities of the co-product might complicate the product separation and the recovery of the chiral amine. Thus, the asymmetric synthesis is generally preferable because a theoretically 100
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Published 07 Jan 2019

Mechanistic studies of an L-proline-catalyzed pyridazine formation involving a Diels–Alder reaction with inverse electron demand

  • Anne Schnell,
  • J. Alexander Willms,
  • S. Nozinovic and
  • Marianne Engeser

Beilstein J. Org. Chem. 2019, 15, 30–43, doi:10.3762/bjoc.15.3

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  • between ketones and aryl-substituted 1,2,4,5-tetrazines which leads to functionalized pyridazines. They also postulated a mechanism (Scheme 1) for the reaction [51]. Based on the knowledge that secondary amines catalyze the formation of enamines from ketones and other carbonyl compounds [33], an initial
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Published 03 Jan 2019

A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

  • Ilya V. Taydakov,
  • Yuliya M. Kreshchenova and
  • Ekaterina P. Dolotova

Beilstein J. Org. Chem. 2018, 14, 3106–3111, doi:10.3762/bjoc.14.290

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  • commercial batches of NaOMe or NaOEt, along with samples freshly prepared in the laboratory. In all the experiments, anhydrous Et2O was used as the solvent and the initial concentration of carbonyl compounds was 0.2 mol/L. Methyl heptafluorobutanoate (2) was chosen as the ester because the corresponding β
  • course of the reaction but significantly facilitates the purification process. The best results were obtained if THF solution of carbonyl compounds was slowly added dropwise to a suspension of NaH in THF, while the temperature was maintained below +5 °C. Upon completion of the condensation, the reaction
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Published 27 Dec 2018

Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion

  • Rudolf Knorr and
  • Barbara Schmidt

Beilstein J. Org. Chem. 2018, 14, 3018–3024, doi:10.3762/bjoc.14.281

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  • -tetramethylindan-2-ylidene)acetonitriles added reversibly to three small aldehydes and two bulky ketones at room temperature. Experimental conditions were determined for transfer of the nucleofugal title carbanion unit between different carbonyl compounds. These readily occurring retro-additions via C–C(O) bond
  • trapped by proton sources such as DMSO or unconsumed 7 to produce 1. As a consequence, the general procedure (GP) of adding carbonyl compounds to deprotonated 1 commends to use an acidic work-up and a strict exclusion of bases that are stronger than diluted aqueous NaHCO3. Benzaldehyde (5) and
  • . Alternatively, carbonyl additions to 2Li might be generally retarded (relative to protonations) on account of the clustered [4] ground state structure of 2Li in solution. Electrophilic cations (Li+ or K+) are not necessary (albeit perhaps helpful) for the addition of the carbanion unit of 2Li or 2K to carbonyl
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Published 11 Dec 2018
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  • these catalysts for extensive reactions, including the synthesis of bis(indolyl)methane derivatives, β-amino carbonyl compounds, 14H-dibenzo[a,j]xanthene derivatives, 1,8-dioxodecahydroacridine derivatives, xanthene derivatives, pyrimido[4,5-b]quinoline derivatives, spiro-isatin derivatives, spiro
  • and 37 from active carbonyl compounds (e.g., isatins 32, acenaphthoquinone (33), and aldehydes 38), a variety of C–H activated acids (cyclohexane-1,3-dione (20a), 5,5-dimethylcyclohexane-1,3-dione (20b), 2-naphthol (23), ethyl acetoacetate (34a), 4-hydroxycoumarin (34b), triacetic acid lactone (34c
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Published 01 Nov 2018

Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source

  • Tetsuaki Fujihara and
  • Yasushi Tsuji

Beilstein J. Org. Chem. 2018, 14, 2435–2460, doi:10.3762/bjoc.14.221

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  • carboxylation of mesityl triflate (5) at 40 °C proceeded successfully, affording 6 in 77% yield (Scheme 6) Carboxylation of α,β-unsaturated nitriles and esters α,β-Unsaturated carbonyl compounds are good substrates for conjugate additions that use a catalytic amount of a metal complex and a stoichiometric
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Published 19 Sep 2018
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