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Journal articles on the topic 'Carbenes (Methylene compounds)'

Author: Grafiati

Published: 4 June 2021

Last updated: 28 July 2024

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1

Kidonakis, Marios, та Manolis Stratakis. "Reduction of the Diazo Functionality of α-Diazocarbonyl Compounds into a Methylene Group by NH3BH3 or NaBH4 Catalyzed by Au Nanoparticles". Nanomaterials 11, № 1 (18 січня 2021): 248. http://dx.doi.org/10.3390/nano11010248.

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Supported Au nanoparticles on TiO2 (1 mol%) are capable of catalyzing the reduction of the carbene-like diazo functionality of α-diazocarbonyl compounds into a methylene group [C=(N2) → CH2] by NH3BH3 or NaBH4 in methanol as solvent. The Au-catalyzed reduction that occurs within a few minutes at room temperature formally requires one hydride equivalent (B-H) and one proton that originates from the protic solvent. This pathway is in contrast to the Pt/CeO2-catalyzed reaction of α-diazocarbonyl compounds with NH3BH3 in methanol, which leads to the corresponding hydrazones instead. Under our stoi

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2

Mbuvi, Harun M., Erik R. Klobukowski, Gina M. Roberts, and L. Keith Woo. "O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources." Journal of Porphyrins and Phthalocyanines 14, no. 03 (March 2010): 284–92. http://dx.doi.org/10.1142/s1088424610001982.

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Iron(III) tetraphenylporphyrin chloride, Fe(TPP)Cl , efficiently catalyzed the insertion of carbenes derived from methyl 2-phenyldiazoacetates into O-H bonds of aliphatic and aromatic alcohols, with yields generally above 80%. Although the analogous N-H insertions are rapid at room temperature, the O-H insertion reactions are slower and required heating in refluxing methylene chloride for about 8 hours using 1.0 mol.% catalyst. Fe(TPP)Cl was also found to be effective for tandem N-H insertion/cyclization reactions when 1,2-diamines and 1,2-alcoholamines were treated with diazo reagents to give

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3

Zoghbi, Michel, та John Warkentin. "Azetinone formation is not competitive with intermolecular reactions of a β-lactam-4-ylidene". Canadian Journal of Chemistry 70, № 11 (1 листопада 1992): 2792–97. http://dx.doi.org/10.1139/v92-355.

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3-Phenoxy-1-phenyl-2-azetidinon-4-ylidene (β-lactam-4-ylidene) 2a, was generated by thermolysis of a spiro-fused β-lactam oxadiazoline precursor (1). Fast 1,2-H migration, a characteristic reaction of singlet carbenes that would convert 2a to 3-phenoxy-1-phenyl-3-azetin-2-one (4a) could not be demonstrated. Added 1, 3-diphenylisobenzofuran (6) did not afford the [4 + 2] cycloadduct (7) expected from 4a but, instead, the isomeric E- and Z-4-[1-(2-benzoylphenyl)-1-phenyl]-methylene-3-phenoxy-1-phenylazetidin-2-ones (9). Those compounds can be rationalized as the products of rearrangement of firs

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4

Kysilka, Ondřej, Markéta Rybáčková, Martin Skalický, Magdalena Kvíčalová, Josef Cvačka, and Jaroslav Kvíčala. "HFPO Trimer-Based Alkyl Triflate, a Novel Building Block for Fluorous Chemistry. Preparation, Reactions and 19F gCOSY Analysis." Collection of Czechoslovak Chemical Communications 73, no. 12 (2008): 1799–813. http://dx.doi.org/10.1135/cccc20081799.

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Triflate 4, CF3(CF2)2O-CF(CF3)CF2O-CF(CF3)CH2-OTf (RFOCH2OTf), of the HFPO trimer-based alcohol 3 (RFOCH2OH) is a novel highly fluorinated building block for fluorous chemistry. In analogy to similar polyfluorinated triflates with methylene spacer, its reactivity is limited to strong and soft nucleophiles. Whereas reactions with cyanide anion, phenolate anion, enolate of diethyl malonate or lithium salt of benzaldehyde bis(phenylsulfanyl)acetal were unsuccessful, the corresponding imidazole 5, iodide 6 or azide 7 were prepared in good yields. Reaction of imidazole 5 with (perfluorohexyl)methyl

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5

Monopoli, Antonio, Pietro Cotugno, Carlo Giorgio Zambonin, Francesco Ciminale, and Angelo Nacci. "Highly selective palladium–benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions." Beilstein Journal of Organic Chemistry 11 (June 10, 2015): 994–99. http://dx.doi.org/10.3762/bjoc.11.111.

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The Pd–benzothiazol-2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji–Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst from Pd2dba3 and 3-methylbenzothiazolium salt V as precursors. A comparison of the performance of benzothiazole carbene with phosphanes and an analogous imidazolium carbene ligand is also proposed.

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6

Amer, Atef Mohamed, Mohamed Fouad Zayed, Ali Deeb, and Ahmed Ali. "Pyridazine derivatives and related compounds. Part 141. Photolysis of 3-diazo-4,5-diphenylpyrazolo[3,4-c]pyridazine." Journal of Chemical Research 2005, no. 10 (October 2005): 643–47. http://dx.doi.org/10.3184/030823405774663011.

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The photochemistry of 3-diazopyrazolopyridazine has been investigated. The irradiation of 3-diazo-4,5-diphenylpyrazolo[3,4-c]pyridazine in various solvents forms a carbene intermediate, which transforms into 3-substituted derivatives. For photolysis in the presence of acetylacetone or ethyl acetoacetate the coupling reactions which occur at the methylene group are faster than carbene formation, and can lead to direct cyclisation into condensed 1,2,4-triazines. Photolysis in the presence of diethyl malonate forms an acyclic hydrazone.

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7

Chetcuti, Michael J., Haithem Naghmouchi, Abdelwaheb Hamdi, and Lydia Karmazin. "Synthesis of Imidazolium Cations Linked to Para-t-Butylcalix[4]arene Frameworks and Their Use as Synthons for Nickel-NHC Complexes Tethered to Calix[4]arenes." Molecules 28, no. 15 (July 27, 2023): 5697. http://dx.doi.org/10.3390/molecules28155697.

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A series of cationic p-tert-butylcalix[4]arenes, with side-arms that are functionalized with imidazolium groups, have been synthesized in good yields. The parent tetrahydroxy para-t-butyl-calix[4]arene was dialkylated at the phenolic hydrogen atoms using α,ω-dibromo-alkanes to yield bis(mono-brominated) alkoxy-chains of variable length. The brominated side-arms in these compounds were then further alkylated with substituted imidazoles (N-methylimidazole, N-(2,4,6-trimethyl-phenyl)imidazole, or N-(2,6-di-isopropylphenyl)imidazole) to yield a series of dicationic calixarenes with two imidazolium

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8

Monopoli, Antonio, Pietro Cotugno, Carlo Giorgio Zambonin, Francesco Ciminale, and Angelo Nacci. "ChemInform Abstract: Highly Selective Palladium-Benzothiazole Carbene-Catalyzed Allylation of Active Methylene Compounds under Neutral Conditions." ChemInform 46, no. 34 (August 2015): no. http://dx.doi.org/10.1002/chin.201534057.

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9

Singh, Shailesh, Jyoti Tiwari, Deepali Jaiswal, Amit Kumar Sharma, Jaya Singh, Vandana Singh, and Jagdamba Singh. "Nucleophilic Acylation with Aromatic Aldehydes to 2 Bromoacetonitrile: An Umpolung Strategy for the Synthesis of Active Methylene Compounds." Current Organic Synthesis 17, no. 7 (October 28, 2020): 518–24. http://dx.doi.org/10.2174/1570179417666200615153536.

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Background: A novel one-pot N-heterocyclic carbene (NHC)-catalysed acylation of 2- bromoacetonitrile with aromatic aldehydes is reported. The protocol involves carbonyl umpolung reactivity of aldehydes in which the carbonyl carbon attacks nucleophilically (as d1 nucleophile) on the electrophilic terminal of 2-bromoacetonitrile to afford 3-aryl-3-oxopropanenitrile. The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Materials and Methods: A flame-dried round bottom flask was charged with Imidazoliu

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10

Terada, Yukiyoshi, Mitsuhiro Arisawa, and Atsushi Nishida. "Cycloisomerization Promoted by the Combination of a Ruthenium–Carbene Catalyst and Trimethylsilyl Vinyl Ether, and its Application in The Synthesis of Heterocyclic Compounds: 3-Methylene-2,3-dihydroindoles and 3-Methylene-2,3-dihydrobenzofurans." Angewandte Chemie International Edition 43, no. 31 (August 6, 2004): 4063–67. http://dx.doi.org/10.1002/anie.200454157.

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11

Terada, Yukiyoshi, Mitsuhiro Arisawa, and Atsushi Nishida. "Cycloisomerization Promoted by the Combination of a Ruthenium–Carbene Catalyst and Trimethylsilyl Vinyl Ether, and its Application in The Synthesis of Heterocyclic Compounds: 3-Methylene-2,3-dihydroindoles and 3-Methylene-2,3-dihydrobenzofurans." Angewandte Chemie 116, no. 31 (August 6, 2004): 4155–59. http://dx.doi.org/10.1002/ange.200454157.

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12

Liu, Mingxin, and Christopher Uyeda. "Redox Approaches to Carbene Generation in Catalytic Cyclopropanation Reactions." Angewandte Chemie, May 16, 2024. http://dx.doi.org/10.1002/ange.202406218.

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Transition metal‐catalyzed carbene transfer reactions have a century‐old history in organic chemistry and are a primary method for the synthesis of cyclopropanes. Much of the work in this field has focused on the use of diazo compounds and related precursors, which can transfer a carbene fragment to a catalyst with concomitant loss of a stable byproduct. Despite the utility of this approach, there are persistent limitations in the scope of viable carbenes, most notably those lacking stabilizing substituents. By coupling carbene transfer chemistry with two‐electron redox cycles, it is possible

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13

Liu, Mingxin, and Christopher Uyeda. "Redox Approaches to Carbene Generation in Catalytic Cyclopropanation Reactions." Angewandte Chemie International Edition, May 16, 2024. http://dx.doi.org/10.1002/anie.202406218.

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Transition metal‐catalyzed carbene transfer reactions have a century‐old history in organic chemistry and are a primary method for the synthesis of cyclopropanes. Much of the work in this field has focused on the use of diazo compounds and related precursors, which can transfer a carbene fragment to a catalyst with concomitant loss of a stable byproduct. Despite the utility of this approach, there are persistent limitations in the scope of viable carbenes, most notably those lacking stabilizing substituents. By coupling carbene transfer chemistry with two‐electron redox cycles, it is possible

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14

Fu, Duo, and Jiaxi Xu. "Synthesis of Sulfo(xo)nium Diacylmethylides." European Journal of Organic Chemistry, April 28, 2024. http://dx.doi.org/10.1002/ejoc.202400390.

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Sulfo(xo)nium diacylmethylides (sulfur ylides) are simple, stable, readily prepared, and versatile synthons. Compared with the sulfo(xo)nium monoacylmethylides, they can be compatible with more rigorous reaction conditions and showcase unique characteristics due to their excellent stability. This concept article provides an account for the syntheses of sulfo(xo)nium diacylmethylides, including the utilization of active methylene compounds, carbene precursors, sulfo(xo)nium monoacylmethylides, and electron‐deficient alkynes as substrates, with discussions on substrate scopes, proposed mechanism

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15

Terada, Yukiyoshi, Mitsuhiro Arisawa, and Atsushi Nishida. "Cycloisomerization Promoted by the Combination of a Ruthenium-Carbene Catalyst and Trimethylsilyl Vinyl Ether, and Its Application in the Synthesis of Heterocyclic Compounds: 3-Methylene-2,3-dihydroindoles and 3-Methylene-2,3-dihydrobenzofurans." ChemInform 35, no. 46 (November 16, 2004). http://dx.doi.org/10.1002/chin.200446039.

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