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Journal articles on the topic 'Benzylen'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

McGeary, Ross, Jed Burns, and Elizabeth Krenske. "Claisen Rearrangements of Benzyl Vinyl Ethers and Heterobenzyl Vinyl Ethers." Synthesis 50, no. 09 (2018): 1750–72. http://dx.doi.org/10.1055/s-0036-1589529.

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The Claisen rearrangement of benzylic substrates (benzyl vinyl ethers) has received considerably less attention than its well-known aliphatic and normal aromatic variants. Here, we review the rearrangement of both benzylic and heterobenzylic substrates, with examples of the reaction’s use in the synthesis of natural products and drug-like molecules.1 Introduction2 Early Attempts at the Benzyl-Claisen Rearrangement3 Successful Benzylic Examples4 Heterobenzylic Examples5 Conclusion

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2

Walji, Dhiran V. B., John M. D. Storey, and William T. A. Harrison. "BenzylN-benzyl-N-(2-formylphenyl)carbamate–benzylN-benzyl-N-(2-carboxyphenyl)carbamate [0.332 (4)/0.668 (4)]." Acta Crystallographica Section E Structure Reports Online 63, no. 4 (2007): o1575—o1576. http://dx.doi.org/10.1107/s1600536807009063.

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3

Suzuki, Koki, Hiroaki Tsuji, and Motoi Kawatsura. "Ruthenium-catalyzed benzylic substitution of benzyl esters with stabilized carbon nucleophiles." Chemical Communications 56, no. 22 (2020): 3273–76. http://dx.doi.org/10.1039/c9cc09899b.

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4

Kitamura, Tsugio. "Synthetic Methods for the Generation and Preparative Application of Benzyne." Australian Journal of Chemistry 63, no. 7 (2010): 987. http://dx.doi.org/10.1071/ch10072.

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Many methods have been developed for generating benzyne. Convenient and reliable precursors extensively studied so far involve benzenediazonium-2-carboxylate and o-dihalobenzenes such as 1,2-bromofluorobenzene and 1,2-dibromobenzene. Recently, in addition to the above precursors, o-(trimethylsilyl)phenyl triflate has been put into frequent use for benzyne reactions, in which benzyne is efficiently generated under mild conditions using fluoride ion. Furthermore, o-(trimethylsilyl)phenyliodonium triflate has been developed as a more efficient benzyne precursor. This mini-review focusses on recen

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5

Urgoitia, Garazi, Ainhoa Maiztegi, Raul SanMartin, María Teresa Herrero, and Esther Domínguez. "Aerobic oxidation at benzylic positions catalyzed by a simple Pd(OAc)2/bis-triazole system." RSC Advances 5, no. 125 (2015): 103210–17. http://dx.doi.org/10.1039/c5ra22251f.

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6

Wentrup, Curt. "The Benzyne Story." Australian Journal of Chemistry 63, no. 7 (2010): 979. http://dx.doi.org/10.1071/ch10179.

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The history of o-benzyne from its early beginnings as an unobservable reactive intermediate until its present status as a very well characterized but still theoretically challenging molecule with important applications in synthesis is reviewed. The m- and p-benzynes, tridehydrobenzenes, and benzdiynes are also known, and p-benzyne is a key intermediate in the action of a potent class of ene-diyne anti-tumour compounds.

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7

Zhang, Lei, and Xile Hu. "Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C–H bonds." Chemical Science 11, no. 39 (2020): 10786–91. http://dx.doi.org/10.1039/d0sc01445a.

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8

Tripathy, Sasmita, Ranga Reddy, and Tony Durst. "Preparation of benzocyclobutenols by low temperature reaction of ketone enolates with benzynes." Canadian Journal of Chemistry 81, no. 9 (2003): 997–1002. http://dx.doi.org/10.1139/v03-099.

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The reaction of benzynes, generated from halobenzenes with lithium tetramethylpipiperide (LTMP) at 40 to 78 °C, with ketone enolates affords benzocyclobutenols in fair to good yields.Key words: benzyne, ketone enolates, anthracenes, benzocyclobutenol, alkoxides.

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9

Wenthold, Paul G. "Thermochemical Properties of the Benzynes." Australian Journal of Chemistry 63, no. 7 (2010): 1091. http://dx.doi.org/10.1071/ch10126.

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The thermochemical properties of the benzynes have been the subject of investigation for nearly 50 years. This work provides an overview and assessment of all the experimental thermochemical properties that have been reported for the benzynes, or can be derived from reported thermochemical data. These properties include enthalpies of formation and thermochemical values that correspond to formation and dissociation of the benzynes by neutral and ionic processes. Thermochemical values are provided for both the ground-state singlet and the excited-state triplet states of the benzynes. The startin

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10

Berger, Anna Lucia, Karsten Donabauer, and Burkhard König. "Photocatalytic Barbier reaction – visible-light induced allylation and benzylation of aldehydes and ketones." Chemical Science 9, no. 36 (2018): 7230–35. http://dx.doi.org/10.1039/c8sc02038h.

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We report a photocatalytic version of the Barbier type reaction using readily available allyl or benzyl bromides and aromatic aldehydes or ketones as starting materials to generate allylic or benzylic alcohols.

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11

Emberson, Kassandra, Ngan Tran, and Costa Metallinos. "Diastereoselective Lithiation of N-Benzyl Pyrroloimidazolones Derived from l-Proline Hydantoin." Synlett 28, no. 20 (2017): 2901–5. http://dx.doi.org/10.1055/s-0036-1591206.

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An N-benzyl pyrroloimidazolone derived from l-proline hydantoin undergoes asymmetric lithiation with n-BuLi/TMEDA in toluene to give products of electrophile quench (E+) that range from 87:13 to 91:9 diastereomeric ratio (dr). All products appear to have the same relative stereochemistry as determined by transmetalation of benzylic stannanes, which gave identical major diastereomers for several products as to what was observed by direct lithiation–substitution of the starting material. X-Ray crystallography of the major diastereomer of the benzophenone adduct established (R)-configuration at t

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12

Ikawa, Takashi, Shigeaki Masuda, Tsuyoshi Nishiyama, Akira Takagi, and Shuji Akai. "Synthesis of Fluorinated Aromatic Compounds by One-Pot Benzyne Generation and Nucleophilic Fluorination." Australian Journal of Chemistry 67, no. 3 (2014): 475. http://dx.doi.org/10.1071/ch13548.

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The fluorination of substituted benzenes using fluoride ions under mild reaction conditions has been one of the most important challenges for the synthesis of biologically active fluorinated aromatic compounds; however, only a few synthetically useful methods are known. In this paper, it is reported that the nucleophilic fluorination of benzynes, generated from either 2-(trialkylsilyl)phenyl nonafluorobutanesulfonates or 2-(trialkylsilyl)phenols, meets this challenge. In particular, the fluorination starting from 2-(trialkylsilyl)phenols for fabricating aryl fluorides involves three sequential

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13

Cahill, Katharine J., Aida Ajaz, and Richard P. Johnson. "New Thermal Routes to ortho-Benzyne." Australian Journal of Chemistry 63, no. 7 (2010): 1007. http://dx.doi.org/10.1071/ch10074.

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There is experimental evidence that intermediate ortho-benzynes can be made by intramolecular [2 + 4] cycloaddition of a 1,3-diyne with an alkyne. Computations by several groups support a concerted mechanism for the cycloaddition of butadiyne with acetylene. High temperature benzyne cycloreversion has also been demonstrated experimentally; this may in fact be a common reaction in hydrocarbon fuel combustion. Following leads from earlier pyrolysis experiments, herein we predict that cycloaddition of benzyne with butadiyne can proceed by a stepwise mechanism to 2,3-naphthyne. However, a slightly

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14

Wang, Tao, Christian Oswood, and Thomas Hoye. "Trapping of Hexadehydro-Diels–Alder Benzynes with Exocyclic, Conjugated Enals as a Route to Fused Spirocyclic Benzopyran Motifs." Synlett 28, no. 20 (2017): 2933–35. http://dx.doi.org/10.1055/s-0036-1589091.

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Exocyclic, conjugated enals react with benzynes generated by heating various triyne-containing substrates to produce spirocyclic benzopyran derivatives. These products are consistent with a mechanistic sequence that involves initial net [2+2] cycloaddition of the benzyne and aldehyde followed by 4π-electrocyclic ring opening and 6π ring closing.

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15

Yuan, Gengyang, Feng Wang, Nickeisha A. Stephenson, et al. "Metal-free 18F-labeling of aryl-CF2H via nucleophilic radiofluorination and oxidative C–H activation." Chemical Communications 53, no. 1 (2017): 126–29. http://dx.doi.org/10.1039/c6cc07913j.

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A metal-free and selective method to form [<sup>18</sup>F]aryl-CF<sub>2</sub>H through nucleophilic radiofluorination of benzyl (pseudo)halides and oxidative C–H activation of benzylic C–H bonds has been developed.

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16

Hřebabecký, Hubert, Martin Dračínský, Armando M. De Palma, Johan Neyts, and Antonín Holý. "Synthesis of novel racemic carbocyclic nucleoside analogues derived from 4,8-dioxatricyclo[4.2.1.03,7]nonane-9-methanol and 4-oxatricyclo[4.3.1.03,7]decane-10-methanol, compounds with activity against Coxsackie viruses." Collection of Czechoslovak Chemical Communications 74, no. 3 (2009): 469–85. http://dx.doi.org/10.1135/cccc2008193.

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(1R*,2R*,3R*,4S*)-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dimethanol (10) and (1R*,2R*,3R*,4S*)-bicyclo[2.2.2]oct-5-ene-2,3-dimethanol (14), which were prepared by the Diels–Alder reaction and subsequent reduction with lithium aluminium hydride, were treated with benzyl azidoformate to give benzylN-[(1R*,2R*,3S*,6S*,7S*,9S*)-9-(hydroxymethyl)-4,8-dioxatricyclo[4.2.1.03,7]nonan-2-yl]carbamate (11) and benzylN-[(1R*,2R*,3R*,6R*,7S*,10S*)-10-(hydroxymethyl)-4-oxatricyclo[4.3.1.03,7]decan-2-yl]carbamate (15). Hydrogenolysis of carbamates11or15afforded (1R*,2R*,3S*,6S*,7S*,9S*)-2-amino-4,8-dioxatricyclo[

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17

Kuroda, Chiaki, Reiri Kobayashi, Saeka Kurebayashi, et al. "Reaction of Aminomalononitrile and Benzylic Compounds as a Plausible Route to Phenylalanine." Natural Product Communications 15, no. 1 (2020): 1934578X2090141. http://dx.doi.org/10.1177/1934578x20901417.

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As a possible route to phenylalanine, reaction of aminomalononitrile with benzylic compounds was studied. 2-Benzyl-2-aminomalononitrile (3) was obtained in a good yield when aminomalononitrile p-toluenesulfonate (1) was treated with benzyl bromide (2) in THF using triethylamine as a base. The reaction proceeded in the presence of water. Compound 3 was hydrolyzed to afford phenylalanine. The aminomalononitrile route can explain the presence of not only 1 methylene in aromatic amino acids, but also α-hydrogen in all 20 proteinogenic amino acids.

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18

Melnicky, Carsten, Ion Neda, and Reinhard Schmutzler. "Darstellung von phosphorylierten Glucosiden durch Umsetzung am Glucosegerüst sowie am Aglycon / Synthesis of Phosphorylated Glucosides through Reaction at the Glucose Framework and at the Aglycon." Zeitschrift für Naturforschung B 54, no. 12 (1999): 1547–52. http://dx.doi.org/10.1515/znb-1999-1212.

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The reaction of Me2P(:X)H [X = O: 1; X = S: 4] with paraformaldehyde furnished the α - hydroxyphosphine oxide 2 and sulfide 5 which, upon treatment with p-toluenesulfonyl chloride, were converted into the tosylated derivatives 3 and 6. The diphosphorylated glucosyl compound 8 was synthesized by reaction of two equivalents of tosylated phosphine oxide 3 with benzyl 4,6- O-benzyliden-α-D-glucopyranoside 7. The spacer phosphorylated glucosyl derivatives 10 and 11 were formed in the reaction of γ -bromopropyl-2,3,4,6-tetra-0 -benzyl-β-D-glucopyranoside 9 with triethylphosphite and triphenylphosphi

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19

Hikawa, Hidemasa, та Isao Azumaya. "Mercaptobenzoic acid-palladium(0) complexes as active catalysts for S-benzylation with benzylic alcohols via (η3-benzyl)palladium(ii) cations in water". Org. Biomol. Chem. 12, № 31 (2014): 5964–72. http://dx.doi.org/10.1039/c4ob00688g.

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Mercaptobenzoic acid-palladium(0) complexes show high catalytic activity for S-benzylation with benzylic alcohols via the (η<sup>3</sup>-benzyl)palladium(ii) cation in water. The catalytic system can be performed using only 2.5 mol% Pd<sub>2</sub>(dba)<sub>3</sub> without the phosphine ligand or other additives.

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20

Cao, Zhi-Chao, Da-Gang Yu, Ru-Yi Zhu, Jiang-Bo Wei, and Zhang-Jie Shi. "Direct cross-coupling of benzyl alcohols to construct diarylmethanes via palladium catalysis." Chemical Communications 51, no. 13 (2015): 2683–86. http://dx.doi.org/10.1039/c4cc10084k.

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A direct arylation to furnish diarylmethanes from benzyl alcohols was realized through Pd(PPh<sub>3</sub>)<sub>4</sub>-catalyzed Suzuki–Miyaura coupling via benzylic C–O activation in the absence of any additives. The arylation is compatible with various functional groups. This development provides an atom- and step-economic way to approach a diarylmethane scaffold under mild and environmentally benign conditions.

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21

Grjol, Blaž, and Marjan Jereb. "Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light." Chemical Papers 75, no. 10 (2021): 5235–48. http://dx.doi.org/10.1007/s11696-021-01711-x.

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AbstractRegioselectivity of visible-light-induced transformations of a range of (hetero)aryl alkyl-substituted ketones bearing several competitive reactive sites (α-carbonyl, benzyl and aromatic ring) with N-bromosuccinimide (NBS) was studied under solvent-free reaction conditions (SFRC) and in the absence of inert-gas atmosphere, radical initiators and catalysts. An 8-W energy-saving household lamp was used for irradiation. Heterogeneous reaction conditions were dealt with throughout the study. All substrates were mono- or dibrominated at the α-carbonyl position, and additionally, some benzyl

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22

Kroskins, Vladislavs, Karina Nikitina, Jevgeņija Lugiņina, and Vitālijs Rjabovs. "Investigation of Carbohydrate C-Silylation with Chlorosilanes." Key Engineering Materials 850 (June 2020): 254–58. http://dx.doi.org/10.4028/www.scientific.net/kem.850.254.

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We studied possibility of silylation of lithiated carbohydrates using chlorosilanes. We observed that after the lithiation, the silylation is concurrent with a protonation reaction. In the case of trimethyl chlorosilane, we achieved 1:1 ratio with 36% isolated yield, while triphenyl chlorosilane gave 1:2 (silylated:reduced) ratio and 4% isolated yield. In the case of benzyl protected carbohydrate, silylation at benzylic position was observed.

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23

Ma, Xiaodong, Jie An, Shihui Luo та ін. "Reductive Deuteration of Aromatic Esters for the Synthesis of α,α-Dideuterio Benzyl Alcohols Using D2O as Deuterium Source". Synlett 32, № 01 (2020): 51–56. http://dx.doi.org/10.1055/s-0040-1705944.

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Abstractα,α-Dideuterio benzyl alcohols are important building blocks for the synthesis of deuterium-labeled medicines and agrochemicals. We have developed the first general single-electron transfer reductive deuteration of readily commercially available aromatic esters for the synthesis of α,α-dideuterio benzyl alcohols using benign D2O and a mild single-electron donor SmI2. This operationally convenient method features very good functional group tolerance and high deuterium incorporations (>95% D2). The potential impact has been exemplified by the synthesis of numerous deuterium labeled bu

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24

Malone, Vincent F., Amy J. Chastain, John T. Ohlsson, Loelle S. Poneleit, Michele Nemecek-Marshall, and Ray Fall. "Characterization of a Pseudomonas putidaAllylic Alcohol Dehydrogenase Induced by Growth on 2-Methyl-3-Buten-2-ol." Applied and Environmental Microbiology 65, no. 6 (1999): 2622–30. http://dx.doi.org/10.1128/aem.65.6.2622-2630.1999.

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ABSTRACT We have been working to develop an enzymatic assay for the alcohol 2-methyl-3-buten-2-ol (232-MB), which is produced and emitted by certain pines. To this end we have isolated the soil bacteriumPseudomonas putida MB-1, which uses 232-MB as a sole carbon source. Strain MB-1 contains inducible 3-methyl-2-buten-1-ol (321-MB) and 3-methyl-2-buten-1-al dehydrogenases, suggesting that 232-MB is metabolized by isomerization to 321-MB followed by oxidation. 321-MB dehydrogenase was purified to near-homogeneity and found to be a tetramer (151 kDa) with a subunit mass of 37,700 Da. It catalyzes

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25

Tunge, Jon, Robert Torregrosa, Shehani Mendis, and Alex Davies. "Palladium-Catalyzed Decarboxylative Benzylation of Acetylides and Enolates." Synthesis 50, no. 16 (2018): 3205–16. http://dx.doi.org/10.1055/s-0037-1609575.

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Benzylic alkylation of enolates and acetylides has been achieved through the use of a decarboxylative benzylation strategy. Previous research in this area is often limited by the need for extended conjugation in the electrophiles that are coupled. Herein, we report that the use of 1,1'-bis(diphenylphosphino)ferrocene (dppf) ligand allows the coupling of simple benzyl electrophiles with enolates, while the use of XPhos ligand promotes the decarboxylative couplings of propiolates.

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26

Arnold, Donald R., A. Martin de P. Nicholas та Kent M. Young. "A comparison of electron spin resonance α- and β-hyperfine coupling constants in para-substituted α-phenethyl radicals". Canadian Journal of Chemistry 64, № 4 (1986): 769–72. http://dx.doi.org/10.1139/v86-124.

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The linear relationship between the electron spin resonance hyperfine coupling constants (hfc) of the α- and β-hydrogens of para-substituted α-phenethyl radicals provides experimental evidence that the magnitude of both the α- and β -hfc is determined largely by the extent of spin delocalization in these benzylic systems. The [Formula: see text] scale, developed using substituted benzyl radicals, is shown to apply to phenethyl radicals as well.

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27

Jones, Elizabeth P., Peter Jones, Andrew J. P. White, and Anthony G. M. Barrett. "Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction." Beilstein Journal of Organic Chemistry 7 (November 25, 2011): 1570–76. http://dx.doi.org/10.3762/bjoc.7.185.

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A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims.

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28

Merkley, Nadine, and John Warkentin. "Benzyloxy(4-substituted benzyloxy)carbenes. Generation from oxadiazolines and fragmentation to radical pairs in solution." Canadian Journal of Chemistry 78, no. 7 (2000): 942–49. http://dx.doi.org/10.1139/v00-078.

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Thermolysis of 2,2-dibenzyloxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline in benzene at 110°C leads to dibenzyloxycarbene. The carbene was trapped with tert-butyl alcohol to afford dibenzyl-tert-butyl orthoformate. In the absence of a trapping agent for the carbene, it fragmented to benzyloxycarbonyl and benzyl radicals, as shown by trapping the latter with TEMPO. In the absence of both TEMPO and tert-butyl alcohol, the radicals were partitioned between coupling to benzyl phenylacetate and decarboxylation, with subsequent formation of bibenzyl. The preferred sense of fragmentation of the analogous car

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29

Bruno, Giuseppe, Santo Lanza, Antonino Giannetto, Alessandro Sacca та Hadi Amiri Rudbari. "Crystal structure of (μ-N,N′-dibenzyldithiooxamidato-κN,S:N′,S′)bis[(η3-crotyl)palladium(II)]". Acta Crystallographica Section E Crystallographic Communications 71, № 2 (2015): m40—m41. http://dx.doi.org/10.1107/s2056989015001292.

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In the centrosymmetric dinuclear title compound, [Pd2(C4H7)2(C16H14N2S2)], the metal atom is η3-coordinated by three C atoms of a crotyl ligand [Pd—C = 2.147 (4), 2.079 (5) and 2.098 (5) Å], the longest distance influenced by the steric interaction with the benzyl substituents of the dibenzyldithiooximidate (DTO) ligand. The Pd—N and Pd—S bonds to this ligand are 2.080 (3) and 2.3148 (9) Å, respectively, completing a square-planar coordination environment for PdII. The benzyl groups are oriented so as to maximize the interaction between a benzylic H atom and an S atom, resulting in a dihedral

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30

Waisser, Karel, Milan Peřina, Věra Klimešová, and Jarmila Kaustová. "On the Relationship between the Structure and Antimycobacterial Activity of Substituted N-Benzylsalicylamides." Collection of Czechoslovak Chemical Communications 68, no. 7 (2003): 1275–94. http://dx.doi.org/10.1135/cccc20031275.

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Sixty-six N-benzylsalicylamides substituted in the acyl moiety in positions 3, 4 or 5 and in position 4 on the benzylic aromatic ring were synthesized. The compounds were tested for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium. To evaluate structure-antimycobacterial activity relationships (QSARs), approaches based on the Free-Wilson as well as a combination of the Free-Wilson and Hansch methods were employed (substituent constants were used to describe the influence of the benzyl substituents, indicator parameters were

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31

Shi, Feng, Jesse P. Waldo, Yu Chen, and Richard C. Larock. "Benzyne Click Chemistry: Synthesis of Benzotriazoles from Benzynes and Azides." Organic Letters 10, no. 12 (2008): 2409–12. http://dx.doi.org/10.1021/ol800675u.

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32

Harder, Sjoerd, Christian Ruspic, Nollaig Ní Bhriain, Frederic Berkermann, and Markus Schürmann. "Benzyl Complexes of Lanthanide(II) and Lanthanide(III) Metals: Trends and Comparisons." Zeitschrift für Naturforschung B 63, no. 3 (2008): 267–74. http://dx.doi.org/10.1515/znb-2008-0307.

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A variety of benzyllanthanide complexes have been prepared by the metathesis reaction of benzylpotassium precursors with lanthanide halides. Syntheses and crystal structures for the following complexes are described: [2-Me2N-α-Me3Si-benzyl]2Eu(II)·(THF)2 (1-Eu), (2-Me2Nbenzyl) 3Ln(III) (2-Ln with Ln = Nd, Sm, Dy, Ho, Yb), (4-R-C6H4CH2)3Ln·(THF)3 (3-Y: Ln = Y, R = H; 3-La: Ln = La, R = tBu). Complexes of types 1 and 2 are thermally robust on account of a stabilization by a benzylic Me3Si substituent and/or intramolecular coordination of the Me2N substituent. Comparison of the crystal structures

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33

Kim, Shokaku, Rikiya Uchiyama, Yoshikazu Kitano, Masahiro Tada, and Kazuhiro Chiba. "Benzylic nitroalkylation by paired electrolysis of benzyl sulfides in nitroalkanes." Journal of Electroanalytical Chemistry 507, no. 1-2 (2001): 152–56. http://dx.doi.org/10.1016/s0022-0728(01)00389-8.

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34

Makida, Yusuke, Kazumi Usui, Satoshi Ueno, and Ryoichi Kuwano. "Palladium-catalyzed Benzylic Substitution of Benzyl Carbonates with Phosphorus Nucleophiles." Chemistry Letters 46, no. 12 (2017): 1814–17. http://dx.doi.org/10.1246/cl.170901.

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35

Keddie, Neil S., Pier Alexandre Champagne, Justine Desroches, Jean-François Paquin, and David O'Hagan. "Stereochemical outcomes of C–F activation reactions of benzyl fluoride." Beilstein Journal of Organic Chemistry 14 (January 9, 2018): 106–13. http://dx.doi.org/10.3762/bjoc.14.6.

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In recent years, the highly polar C–F bond has been utilised in activation chemistry despite its low reactivity to traditional nucleophiles, when compared to other C–X halogen bonds. Paquin’s group has reported extensive studies on the C–F activation of benzylic fluorides for nucleophilic substitutions and Friedel–Crafts reactions, using a range of hydrogen bond donors such as water, triols or hexafluoroisopropanol (HFIP) as the activators. This study examines the stereointegrity of the C–F activation reaction through the use of an enantiopure isotopomer of benzyl fluoride to identify whether

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36

Sterckx, Hans, Johan De Houwer, Carl Mensch, Wouter Herrebout, Kourosch Abbaspour Tehrani, and Bert U. W. Maes. "Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen." Beilstein Journal of Organic Chemistry 12 (January 27, 2016): 144–53. http://dx.doi.org/10.3762/bjoc.12.16.

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The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP–MS analysis of the purified reaction products revealed that the base me

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Pfaff, Dominik, Gregor Nemecek, and Joachim Podlech. "A Lewis acid-promoted Pinner reaction." Beilstein Journal of Organic Chemistry 9 (August 2, 2013): 1572–77. http://dx.doi.org/10.3762/bjoc.9.179.

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Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is similarly possible. Phenols are not acylated under these reaction conditions. The method has been used for the first total synthesis of the natural product monaspilosin. In the reaction of benzyl alcohol

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38

Safa, Kazem D., Hassan Abbasi, Reza Teimuri-Mofrad, and Farzaneh A. Charandabi. "[Tris(alkoxydimethylsilyl)methyl]alkylferrocenes as New Ferrocenyl Multifunctional Silyl Ethers." Australian Journal of Chemistry 67, no. 5 (2014): 784. http://dx.doi.org/10.1071/ch13632.

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[Tris(trimethylsilyl)methyl]alkylferrocenes and [tris(dimethylsilyl)methyl]alkylferrocenes were synthesized by treatment of tris(trimethylsilyl)methyllithium and tris(dimethylsilyl)methyllithium in THF with 3-bromopropylferrocene or 4-bromobutylferrocene at 0°C. [Tris(alkoxydimethylsilyl)methyl]alkylferrocenes were obtained by dehydrocoupling with various aliphatic and benzylic alcohols in the presence of the Karstedt catalyst (platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane in xylene) in good to excellent yields. 4-[Tris(benzyloxydimethylsilyl)methyl]butylferrocene was also prepared fro

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Dachriyanus, Melvyn V. Sargent, Brian W. Skelton, and Allan H. White. "Cycloadducts of Benzynes and 3,4-Dimethoxyfuran." Australian Journal of Chemistry 53, no. 4 (2000): 267. http://dx.doi.org/10.1071/ch99116.

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Cycloaddition between benzyne and 3,4-dimethoxyfuran (1) yielded 2,3-dimethoxy-1,4-dihydro-1,4- epoxynaphthalene (3) which was unusually labile. On chromatography and exposure to air, it yielded (1α,3β,4α)-3-methoxy-3,4-dihydro-1,4-epoxynaphthalen-2(1H)-one (4) and (5α,5aβ,6aα,7β,12β,12aα,13aβ,14α)-6a,12a,13a-tri-methoxy-6a,7,12,12a,13a,14-hexahydro-5,14:7,12-diepoxydinaphtho[2,3-b:2′,3′-e][1,4]dioxin-5a(5H)-ol (19). A single-crystal X-ray structure determination was performed on compound (19). The chemistry of the ketone (4) was investigated. Cycloadditions were also carried out with 3,4-dime

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40

Niwa, Takashi, Hideki Yorimitsu, and Koichiro Oshima. "Palladium-catalyzed benzylic direct arylation of benzyl sulfones with aryl halides." Tetrahedron 65, no. 10 (2009): 1971–76. http://dx.doi.org/10.1016/j.tet.2009.01.030.

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Poverenov, Elena, Irena Efremenko, Gregory Leitus, Jan M. L. Martin та David Milstein. "Benzyl Cation Stabilized by Metal Complexation. Relative Stability of Coordinated Methylene Arenium, π-Benzylic, and σ-Benzylic Structures". Organometallics 32, № 17 (2013): 4813–19. http://dx.doi.org/10.1021/om400523f.

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42

Yokoyama, T., H. M. Chang, R. S. Reiner, R. H. Atalla, I. A. Weinstock, and J. F. Kadla. "Polyoxometalate oxidation of non-phenolic lignin subunits in water: Effect of substrate structure on reaction kinetics." Holzforschung 58, no. 2 (2004): 116–21. http://dx.doi.org/10.1515/hf.2004.016.

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Summary The effect of lignin-biopolymer structure on the mechanism of its oxidative depolymerization by polyoxometalates (POMs) was investigated by reacting an equilibrated POM ensemble with a series of ring-substituted benzyl alcohols. Under anaerobic conditions in mixed water/methanol, observed pseudo-first order reaction rates (150°C) of 8.96 × 10−3 and 4.89 × 10−3 sec−1 were obtained for oxidations of 1-(3,4-dimethoxyphenyl) ethanol (1) and 1-(3,4,5-trimethoxyphenyl)ethanol (2), respectively. Organic products from the oxidation of 2 (95% recovery) indicate the reaction proceeds via success

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43

Rueffer, Martina, and Meinhart H. Zenk. "Distant Precursors of Benzylisoquinoline Alkaloids and their Enzymatic Formation." Zeitschrift für Naturforschung C 42, no. 4 (1987): 319–32. http://dx.doi.org/10.1515/znc-1987-0402.

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The incorporation rates of labelled tyrosine, DOPA. tyramine. and dopamine have been investigated during the in vivo formation of the protoberberine alkaloid, jatrorrhizine, in callus cultures of Berberis canadensis. While tyrosine was equally well incorporated into both the isoquinoline (54%) and benzyl (46%) portions of the alkaloid, DOPA was almost exclusively (91%) transformed into the isoquinoline moiety. However, tyramine (25%) and to a lesser extent, dopamine (15%) were incorporated into the aldehyde-derived, benzylic half of the isoquinoline molecule as well. In order to investigate

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44

Cowton, E. Lucy M., Susan E. Gibson (née Thomas), Michael J. Schneider, and Mark H. Smith. "Chiral base-mediated benzylic functionalisation of (alkyl benzyl ether)tricarbonylchromium(0) complexes." Chem. Commun., no. 7 (1996): 839–40. http://dx.doi.org/10.1039/cc9960000839.

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45

Curtis, Abigale J., Megan C. Shirk, and Ray Fall. "Allylic or Benzylic Stabilization Is Essential for Catalysis by Bacterial Benzyl Alcohol Dehydrogenases." Biochemical and Biophysical Research Communications 259, no. 1 (1999): 220–23. http://dx.doi.org/10.1006/bbrc.1999.0738.

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46

Tsuji, Hiroaki, Koki Suzuki, and Motoi Kawatsura. "Ruthenium-catalyzed stereospecific benzylic alkylation of optically active benzyl esters with malonate nucleophiles." Tetrahedron Letters 69 (April 2021): 152947. http://dx.doi.org/10.1016/j.tetlet.2021.152947.

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47

Gui, Yang, and Shi-Kai Tian. "Stereospecific Nucleophilic Substitution of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Benzyne." Organic Letters 19, no. 7 (2017): 1554–57. http://dx.doi.org/10.1021/acs.orglett.7b00365.

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48

Brunner, Henri, Friedrich Maiterth, and Barbara Treittinger. "Synthese und Antitumoraktivität von [1,2-Diamino-1-(p-hydroxy)benzyl]ethan(dichloro)platin(II)-KomplexenSynthesis and Antitumor Activity of [1,2-Diamino-1-(p-hydroxy)benzyl]ethane(dichloro)platinum(II) Complexes." Zeitschrift für Naturforschung B 47, no. 7 (1992): 942–46. http://dx.doi.org/10.1515/znb-1992-0708.

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The complexes [1,2-diamino-l-(p-hydroxy)benzyl-1-(methyl, ethyl, and phenyl)]ethane-(dichloro)platinum(II) were synthesized and characterized. The benzylic p-hydroxy group of the 1,2-diaminoethane ligand leads to good water-solubility of the complexes. The ligands were synthesized in a Strecker-type reaction, starting from the corresponding p-methoxybenzylketones. The amino nitriles were reduced to the diamines. Finally, the p-methoxy groups were converted into hydroxy groups by ether cleavage. For the preparation of the complexes, K2PtCl4 was added to the ligands. The antitumor activity of th

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Liu, Mingyang, Zhanrong Zhang, Huizhen Liu, Zhenbing Xie, Qingqing Mei, and Buxing Han. "Transformation of alcohols to esters promoted by hydrogen bonds using oxygen as the oxidant under metal-free conditions." Science Advances 4, no. 10 (2018): eaas9319. http://dx.doi.org/10.1126/sciadv.aas9319.

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One-pot oxidative transformation of alcohols into esters is very attractive, but metal-based catalysts are used in the reported routes. We discovered that the basic ionic liquid 1-ethyl-3-methylimidazolium acetate ([EMIM] OAc) could effectively catalyze this kind of reaction using O2 as an oxidant without any other catalysts or additives. The oxidative self-esterification of benzylic alcohols or aliphatic alcohols and cross-esterification between benzyl alcohols and aliphatic alcohols could all be achieved with high yields. Detailed study revealed that the cation with acidic proton and basic a

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Balakshin, Mikhail Yu, Ewellyn A. Capanema, and Hou-min Chang. "MWL fraction with a high concentration of lignin-carbohydrate linkages: Isolation and 2D NMR spectroscopic analysis." Holzforschung 61, no. 1 (2007): 1–7. http://dx.doi.org/10.1515/hf.2007.001.

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Abstract A preparation enriched in lignin-carbohydrate fragments (LCC-AcOH) was isolated in the course of purification of loblolly pine crude milled wood lignin (MWL). The preparation contained approximately equal amounts of lignin and carbohydrates, with high amounts of arabinose and galactose compared to their levels in wood. LCC-AcOH was investigated by 2D 1H-13C (HMQC and HMBC) correlation NMR techniques and quantitative 13C NMR. The HMQC spectra allowed direct detection of phenyl glycoside, ester and benzyl ether lignin-carbohydrates linkages in high amounts. The assignment of these struc

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