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Journal articles on the topic 'Carbon metal bond cleavage'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Kakiuchi, Fumitoshi, and Takuya Kochi. "Transition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage." Synthesis 2008, no. 19 (September 5, 2008): 3013–39. http://dx.doi.org/10.1055/s-2008-1067256.

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2

Zhu, Chunyin, Wei Wei, Peng Du, and Xiaobing Wan. "Metal free amide synthesis via carbon–carbon bond cleavage." Tetrahedron 70, no. 51 (December 2014): 9615–20. http://dx.doi.org/10.1016/j.tet.2014.11.003.

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3

Murakami, Masahiro, and Takanori Matsuda. "ChemInform Abstract: Metal-Catalyzed Cleavage of Carbon-Carbon Bond." ChemInform 42, no. 20 (April 21, 2011): no. http://dx.doi.org/10.1002/chin.201120217.

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4

Wang, Yifan, and Aimin Liu. "Carbon–fluorine bond cleavage mediated by metalloenzymes." Chemical Society Reviews 49, no. 14 (2020): 4906–25. http://dx.doi.org/10.1039/c9cs00740g.

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Organic fluorochemicals are widely distributed in the environment, causing ecological and health concerns. However, defluorination is a challenging process. This article summarizes the defluorination mechanisms learned from metal-containing enzymes.

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5

Masarwa, Ahmad, and Ilan Marek. "Selectivity in Metal-Catalyzed CarbonCarbon Bond Cleavage of Alkylidenecyclopropanes." Chemistry - A European Journal 16, no. 32 (August 17, 2010): 9712–21. http://dx.doi.org/10.1002/chem.201001246.

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6

Edelbach, Brian L., A. K. Fazlur Rahman, Rene J. Lachicotte, and William D. Jones. "Carbon−Fluorine Bond Cleavage by Zirconium Metal Hydride Complexes." Organometallics 18, no. 16 (August 1999): 3170–77. http://dx.doi.org/10.1021/om9902481.

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7

Zhu, Chunyin, Wei Wei, Peng Du, and Xiaobing Wan. "ChemInform Abstract: Metal Free Amide Synthesis via Carbon-Carbon Bond Cleavage." ChemInform 46, no. 18 (April 16, 2015): no. http://dx.doi.org/10.1002/chin.201518092.

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8

Darensbourg, Marcetta Y., and Donald J. Darensbourg. "The Chemistry of the Metal-Carbon Bond. Volume 2. The Nature and Cleavage of Metal-Carbon Bonds." Organometallics 5, no. 4 (April 1986): 828. http://dx.doi.org/10.1021/om00135a600.

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9

Eaborn, Colin. "The Chemistry of the Metal—Carbon Bond. Volume 2, The Nature and Cleavage of Carbon—Metal Bonds." Journal of Organometallic Chemistry 288, no. 3 (June 1985): c61. http://dx.doi.org/10.1016/0022-328x(85)80139-x.

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10

Murakami, Masahiro, and Takanori Matsuda. "Metal-catalysed cleavage of carbon–carbon bonds." Chem. Commun. 47, no. 4 (2011): 1100–1105. http://dx.doi.org/10.1039/c0cc02566f.

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11

Masarwa, Ahmad, and Ilan Marek. "ChemInform Abstract: Selectivity in Metal-Catalyzed Carbon-Carbon Bond Cleavage of Alkylidenecyclopropanes." ChemInform 41, no. 52 (December 2, 2010): no. http://dx.doi.org/10.1002/chin.201052230.

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12

Shimada, Tomohiro, and Yoshinori Yamamoto. "Carbon−Carbon Bond Cleavage of Diynes through the Hydroamination with Transition Metal Catalysts." Journal of the American Chemical Society 125, no. 22 (June 2003): 6646–47. http://dx.doi.org/10.1021/ja034105o.

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13

Lou, Jiang, Quannan Wang, Ping Wu, Hongmei Wang, Yong-Gui Zhou, and Zhengkun Yu. "Transition-metal mediated carbon–sulfur bond activation and transformations: an update." Chemical Society Reviews 49, no. 13 (2020): 4307–59. http://dx.doi.org/10.1039/c9cs00837c.

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This review summarizes the advances in transition-metal-catalyzed cross-coupling via carbon–sulfur bond activation and cleavage since late 2012 as an update of the critical review published in early 2013 (Chem. Soc. Rev., 2013, 42, 599–621).

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14

Yu, Qing, Yating Zhang, and Jie-Ping Wan. "Ambient and aerobic carbon–carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis." Green Chemistry 21, no. 12 (2019): 3436–41. http://dx.doi.org/10.1039/c9gc01357a.

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With a low loading of Rose Bengal (1 mol%) and green LED irradiation, α-ketoesters are efficiently synthesized with excellent product diversity and selectivity via the ambient cleavage of the enaminone CC double bond.

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15

Adams, Richard D., O.-Sung Kwon, and Joseph L. Perrin. "Cleavage of Carbon−Sulfur Bonds by Triosmium Clusters. Evidence for a Novel Two-Center Mechanism Predicated on Metal−Metal Bond Cleavage." Organometallics 19, no. 12 (June 2000): 2246–48. http://dx.doi.org/10.1021/om0000111.

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16

Cryle, Max J., and James J. De Voss. "Carbon–carbon bond cleavage by cytochrome P450BioI(CYP107H1)." Chem. Commun., no. 1 (2004): 86–87. http://dx.doi.org/10.1039/b311652b.

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17

Oshima, Koichiro. "Highly Selective Organic Synthesis Based on Controlled Cleavage of Carbon-Metal Bond." Journal of Synthetic Organic Chemistry, Japan 64, no. 1 (2006): 2–13. http://dx.doi.org/10.5059/yukigoseikyokaishi.64.2.

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18

Black, DS, GB Deacon, and GL Edwards. "Observations on the Mechanism of Halogen-Bridge Cleavage by Unidentate Ligands in Square Planar Palladium and Platinum Complexes." Australian Journal of Chemistry 47, no. 2 (1994): 217. http://dx.doi.org/10.1071/ch9940217.

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Cyclo-palladation and - platination of nitrogen donor ligands lead to insoluble μ- chloro dimers which give μ- bromo and μ- iodo dimers on metathesis with the appropriate lithium halide. Addition of pyridine or 2,6-dimethylpyridine to the cyclopalladated dimers gives monomeric complexes with the halogen trans to the metal-carbon bond, whereas addition of 2,6-dimethylpyridine to the cycloplatinated complexes gives the isomer with the halogen cis to the metal-carbon bond. The results are discussed in terms of the mechanism of the bridge cleavage reaction.

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19

Soares and Castellã Pergher. "Influence of the Brønsted Acidity on the Ring Opening of Decalin for Pt-USY Catalysts." Catalysts 9, no. 10 (September 20, 2019): 786. http://dx.doi.org/10.3390/catal9100786.

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A challenging hot topic faced by the oil refinery industry is the upgrading of low-quality distillate fractions, such as light cycle oil (LCO), in order to meet current quality standards for diesel fuels. An auspicious technological alternative entails the complete saturation of the aromatic structures followed by the selective cleavage of endocyclic carbon-carbon bonds in the formed naphthenic rings (selective ring opening—SRO). This work reports the influence of Brønsted acid sites of platinum-ultra stable Y zeolite (Pt-USY) catalysts in the SRO of decalin as a model naphthenic feed. A maximum combined yield to selective ring opening products (ROP: C10-alkylcycloalkanes + OCD: C10-alkanes) as high as 28.6 wt% was achieved for 1.6Pt-NaUSY-im catalyst. The molar carbon distribution curve of the hydrocracked (C9-) products varied from M-shaped for 1.4Pt-USY-im catalyst, indicating mainly C–C bond cleavage of the ring opening products with one remaining naphthenic ring via carbocations and the paring reaction, to not M-shaped for the 1.6Pt-NaUSY-im catalyst, where carbon-carbon bond cleavage occurs preferentially through a hydrogenolysis mechanism on metal sites. High (hydro)thermal stability and secondary mesoporosity of the 1.6Pt-NaUSY-im catalysts make this system highly prospective for upgrading low-quality real distillate feeds.

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20

Wahba, Haytham, Ahmed Mansour, Julien Vanasse, Laurent Cappadocia, Jurgen Sygusch, Kevin Wilkinson, and James Omichinski. "The organomercurial lyase Merb possesses unique metal-binding properties." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C1680. http://dx.doi.org/10.1107/s2053273314083193.

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Select bacterial strains survive in mercury-contaminated environments due to acquisition of a transferable genetic element known as the mer operon. The mer operon typically encodes for a series of proteins that includes two enzymes, MerA and MerB. The organomercurial lyase (MerB) cleaves carbon-mercury bonds of organomercurial compounds yielding ionic mercury Hg (II) and a reduced-carbon compound. The Hg (II) ion product remains bounds until it is shuttled directly to the mercuric ion reductase (MerA) to be reduced. Based on NMR spectroscopy and X-ray crystallography studies1, we have determined that Cys96, Asp99 and Cys159 of E. Coli MerB form a catalytic triad required for cleavage of the carbon-Hg bond and binding of the Hg (II) ion product. The three catalytic residues are conserved in 61 of 65 known variants of MerB and the four remaining variants retain both cysteine residues, but contain a serine in place of Asp99. Given its unique activity, we have examined the role of serine as a catalytic residue and the ability of MerB to cleave other organometals such as organotin (known substrates or inhibitors) and organolead compounds. Soaking MerB crystals with either dimethyltindibromide or trimethylleadchloride compound indicates that MerB crystals have the capacity to cleave both carbon-Sn and carbon-Pb bonds, and we have determined crystal structures of a MerB-Sn and a MerB-Pb complex. Furthermore, substitution of Ser for Asp99 (MerB D99S) in E. coli MerB alters the metal-binding specificity, as MerB D99S chelated an unknown metal during its purification. X-ray crystallography, ICP-MS and electron paramagnetic resonance (EPR) studies were performed to identify the unknown metal and the results of these studies will be presented. Given that mercury contaminated sites are often contaminated with other heavy metals, these studies indicate that other heavy metals may have important implications when using MerA and MerB in bioremediation of organomercurial compounds.

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21

Zhu, Chunyin, Wei Wei, Peng Du, and Xiaobing Wan. "Corrigendum to “Metal free amide synthesis via carbon–carbon bond cleavage” [Tetrahedron 70 (2014) 9615–9620]." Tetrahedron 72, no. 5 (February 2016): 779. http://dx.doi.org/10.1016/j.tet.2015.12.033.

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22

Suggs, J. William, and Chul-Ho Jun. "Metal-catalysed alkyl ketone to ethyl ketone conversions in chelating ketones via carbon–carbon bond cleavage." J. Chem. Soc., Chem. Commun., no. 2 (1985): 92–93. http://dx.doi.org/10.1039/c39850000092.

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23

Garrou, Philip E. "Transition-metal-mediated phosphorus-carbon bond cleavage and its relevance to homogeneous catalyst deactivation." Chemical Reviews 85, no. 3 (June 1985): 171–85. http://dx.doi.org/10.1021/cr00067a001.

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24

Ng, Chi Tat, Xiaojun Wang, and Tien Yau Luh. "Transition metal-promoted reactions. Part 21. Tungsten hexacarbonyl-mediated carbon-sulfur bond cleavage reactions." Journal of Organic Chemistry 53, no. 11 (May 1988): 2536–39. http://dx.doi.org/10.1021/jo00246a024.

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25

Fujiwara, Shin-ichi, Masashi Toyofuku, Hitoshi Kuniyasu, and Nobuaki Kambe. "Transition-metal-catalyzed cleavage of carbon–selenium bond and addition to alkynes and allenes." Pure and Applied Chemistry 82, no. 3 (February 18, 2010): 565–75. http://dx.doi.org/10.1351/pac-con-09-11-13.

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This account summarizes our recent results on transition-metal-catalyzed cleavage of C–Se bond and addition to unsaturated hydrocarbons such as alkynes and allenes. Pd(0)-catalyzed intramolecular carbamoselenation of alkynes forms four- to eight-membered α-alkylidenelactams. Interestingly, four-membered ring formation is faster than five- and six-membered ring formation. Intramolecular vinylselenation of suitably structured alkynes offers pathways to conjugated δ-lactam frameworks. Electron-withdrawing groups on the vinyl moiety are essential to promote this reaction. Intermolecular 1,2-addition of selenol esters onto allenes proceeds with excellent regioselectivity and high stereoselectivity in the presence of a Pd(0) catalyst, producing functionalized allyl selenides. In addition, Pd(0)-catalyzed intramolecular selenocarbamoylation of allenes gives α,β-unsaturated γ- and δ-lactams with perfect regioselectivity. The scope and limitations, as well as reaction pathways, are discussed.

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26

Lo, Yih-Hsing, Ming-Che Li, Li-Yu Huang, and Guan-Jie Hung. "Isolation of ruthenium formyl complexes: Insight into the metal-mediated cleavage reaction of carbon-carbon triple bond." Journal of Organometallic Chemistry 830 (February 2017): 109–12. http://dx.doi.org/10.1016/j.jorganchem.2016.12.014.

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27

Rahman, Md Mahbubur, Guangchen Li, and Michal Szostak. "Thioesterification and Selenoesterification of Amides via Selective N–C Cleavage at Room Temperature: N–C(O) to S/Se–C(O) Interconversion." Synthesis 52, no. 07 (February 25, 2020): 1060–66. http://dx.doi.org/10.1055/s-0039-1690055.

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The direct nucleophilic addition to amides represents an attractive methodology in organic synthesis that tackles amidic resonance by ground-state destabilization. This approach has been recently accomplished with carbon, nitrogen and oxygen nucleophiles. Herein, we report an exceedingly mild method for the direct thioesterification and selenoesterification of amides by selective N–C(O) bond cleavage in the absence of transition metals. Acyclic amides undergo N–C(O) to S/Se–C(O) interconversion to give the corresponding thioesters and selenoesters in excellent yields at room temperature via a tetrahedral intermediate pathway (cf. an acyl metal).

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28

Lamont, Laurie J., and Donald R. Arnold. "The effects of metal salts on the photosensitized (electron transfer) carbon–carbon bond cleavage of the 2,2-diphenylethyl ether system." Canadian Journal of Chemistry 68, no. 3 (March 1, 1990): 390–93. http://dx.doi.org/10.1139/v90-059.

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Irradiation of an acetonitrile solution of para-dicyanobenzene (1), 3,3-diphenyltetrahydrofuran (2), and magnesium perchlorate leads to the formation of 4,4-diphenyl-1,3-dioxane (7). Similarly, irradiation of an acetonitrile solution of 1, methyl 2,2-diphenylcyclopentyl ether (5), and magnesium perchlorate leads to the formation of 6,6-diphenyl-2-methoxytetrahydropyran (8). The mechanism proposed for these reactions involves formation of the radical cations [Formula: see text] and [Formula: see text] with the first excited singlet state of 1 acting as the photosensitizer (electron transfer). The radical cations [Formula: see text] and [Formula: see text] then cleave to give 1,5 radical cations. Reaction of the cationic site with water, followed by futher oxidation of the radical site by the perchlorate anion, gives the diphenylalkyl carbocation that can cyclize via a six-membered intermediate to the observed products 7 and 8. While the addition of other perchlorate salts (lithium and tetra-n-butylammonium) also lead to the formation of 7 and 8, lithium trifluoroacetate is ineffective. The proposal that water is involved as the nucleophile is supported by incorporation of 17O in the products 7 and 8 when 17O-enriched water was added to the reaction mixture. Keywords: photosensitization, electron transfer, radical cations, bond cleavage, 2,2-diphenylethyl ether.

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29

Luh, Tien Yau, and Chi Sang Wong. "Transition-metal promoted reactions. 12. Molybdenum hexacarbonyl-promoted reductive cleavage of the carbon-sulfur bond." Journal of Organic Chemistry 50, no. 25 (December 1985): 5413–15. http://dx.doi.org/10.1021/jo00225a091.

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30

Srivastava, R. S. "Carbon-oxygen bond cleavage in allylic esters promoted by low-valent transition-metal hydride complexes." Applied Organometallic Chemistry 7, no. 8 (December 1993): 607–11. http://dx.doi.org/10.1002/aoc.590070803.

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31

Rohmer, Marie-Madeleine. "Photochemical cleavage of the metal—carbon bond in aluminium porphyrins: Insights from ab initio calculations." Chemical Physics Letters 157, no. 3 (May 1989): 207–10. http://dx.doi.org/10.1016/0009-2614(89)87235-5.

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32

Boltersdorf, Jonathan, Asher C. Leff, Gregory T. Forcherio, and David R. Baker. "Plasmonic Au–Pd Bimetallic Nanocatalysts for Hot-Carrier-Enhanced Photocatalytic and Electrochemical Ethanol Oxidation." Crystals 11, no. 3 (February 25, 2021): 226. http://dx.doi.org/10.3390/cryst11030226.

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Gold–palladium (Au–Pd) bimetallic nanostructures with engineered plasmon-enhanced activity sustainably drive energy-intensive chemical reactions at low temperatures with solar simulated light. A series of alloy and core–shell Au–Pd nanoparticles (NPs) were prepared to synergistically couple plasmonic (Au) and catalytic (Pd) metals to tailor their optical and catalytic properties. Metal-based catalysts supporting a localized surface plasmon resonance (SPR) can enhance energy-intensive chemical reactions via augmented carrier generation/separation and photothermal conversion. Titania-supported Au–Pd bimetallic (i) alloys and (ii) core–shell NPs initiated the ethanol (EtOH) oxidation reaction under solar-simulated irradiation, with emphasis toward driving carbon–carbon (C–C) bond cleavage at low temperatures. Plasmon-assisted complete oxidation of EtOH to CO2, as well as intermediary acetaldehyde, was examined by monitoring the yield of gaseous products from suspended particle photocatalysis. Photocatalytic, electrochemical, and photoelectrochemical (PEC) results are correlated with Au–Pd composition and homogeneity to maintain SPR-induced charge separation and mitigate the carbon monoxide poisoning effects on Pd. Photogenerated holes drive the photo-oxidation of EtOH primarily on the Au-Pd bimetallic nanocatalysts and photothermal effects improve intermediate desorption from the catalyst surface, providing a method to selectively cleave C–C bonds.

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33

Robertson, J. H. "The chemistry of the metal-carbon bond. Vol.2. The nature and cleavage of metal-carbon bonds edited by F. R. Hartley and S. Patai." Acta Crystallographica Section B Structural Science 41, no. 6 (December 1, 1985): 456. http://dx.doi.org/10.1107/s0108768185002543.

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34

Werner, Helmut. "Book Review: The Chemistry of the Metal-Carbon Bond. Vol. 2: The Nature and Cleavage of Carbon-Metal Bonds. Vol. 3: Carbon-Carbon Bond Formation using Organometallic Compounds. Edited by F. R. Hartley and S. Patai." Angewandte Chemie International Edition in English 25, no. 10 (October 1986): 945–46. http://dx.doi.org/10.1002/anie.198609451.

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35

Jouikov, Viatcheslav, and Jacques Simonet. "Electrochemical Cleavage of Alkyl Carbon-Halogen Bonds at Carbon-Metal and Metal-Carbon Substrates: Catalysis and Surface Modification." Journal of The Electrochemical Society 160, no. 7 (2013): G3008—G3013. http://dx.doi.org/10.1149/2.002307jes.

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36

Burns, Brendan P., George L. Mendz, and Stuart L. Hazell. "A Novel Mechanism for Resistance to the Antimetabolite N -Phosphonoacetyl-l-Aspartate by Helicobacter pylori." Journal of Bacteriology 180, no. 21 (November 1, 1998): 5574–79. http://dx.doi.org/10.1128/jb.180.21.5574-5579.1998.

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ABSTRACT The mechanism of resistance toN-phosphonoacetyl-l-aspartate (PALA), a potent inhibitor of aspartate carbamoyltransferase (which catalyzes the first committed step of de novo pyrimidine biosynthesis), inHelicobacter pylori was investigated. At a 1 mM concentration, PALA had no effects on the growth and viability ofH. pylori. The inhibitor was taken up by H. pylori cells and the transport was saturable, with aKm of 14.8 mM and aV max of 19.1 nmol min−1 μl of cell water−1. By 31P nuclear magnetic resonance (NMR) spectroscopy, both PALA and phosphonoacetate were shown to have been metabolized in all isolates of H. pyloristudied. A main metabolic end product was identified as inorganic phosphate, suggesting the presence of an enzyme activity which cleaved the carbon-phosphorus (C-P) bonds. The kinetics of phosphonate group cleavage was saturable, and there was no evidence for substrate inhibition at higher concentrations of either compound. C-P bond cleavage activity was temperature dependent, and the activity was lost in the presence of the metal chelator EDTA. Other cleavages of PALA were observed by 1H NMR spectroscopy, with succinate and malate released as main products. These metabolic products were also formed when N-acetyl-l-aspartate was incubated with H. pylori lysates, suggesting the action of an aspartase. Studies of the cellular location of these enzymes revealed that the C-P bond cleavage activity was localized in the soluble fraction and that the aspartase activity appeared in the membrane-associated fraction. The results suggested that the twoH. pylori enzymes transformed the inhibitor into noncytotoxic products, thus providing the bacterium with a mechanism of resistance to PALA toxicity which appears to be unique.

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37

Thornton, Todd A., Gerald A. Ross, Dilip Patil, Kenichi Mukaida, Jeffrey O. Warwick, Neil F. Woolsey, and Duane E. Bartak. "Carbon-oxygen bond-cleavage reactions by electron transfer. 4. Electrochemical and alkali-metal reductions of phenoxynaphthalenes." Journal of the American Chemical Society 111, no. 7 (March 1989): 2434–40. http://dx.doi.org/10.1021/ja00189a010.

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38

Park, Soonheum, Marie Pontier-Johnson, and D. Max Roundhill. "Regioselective carbon-fluorine bond cleavage reactions from the interaction of transition metal fluorocarbon complexes with nucleophiles." Inorganic Chemistry 29, no. 14 (July 1990): 2689–97. http://dx.doi.org/10.1021/ic00339a028.

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39

Fujiwara, Shin-ichi, Masashi Toyofuku, Hitoshi Kuniyasu, and Nobuaki Kambe. "ChemInform Abstract: Transition Metal Catalyzed Cleavage of Carbon-Selenium Bond and Addition to Alkynes and Allenes." ChemInform 41, no. 35 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.201035237.

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40

KONDO, Teruyuki, and Take-aki MITSUDO. "Transition Metal Complex-Catalyzed Selective Cleavage of Carbon-Carbon Bonds: A .BETA.-Carbon Elimination Reaction." Journal of Synthetic Organic Chemistry, Japan 57, no. 6 (1999): 552–58. http://dx.doi.org/10.5059/yukigoseikyokaishi.57.552.

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41

Nishikawa, Tsuyoshi, Arihiro Kanazawa, and Sadahito Aoshima. "Metal-free photoinitiated controlled cationic polymerization of isopropyl vinyl ether using diaryliodonium salts." Polymer Chemistry 10, no. 9 (2019): 1056–61. http://dx.doi.org/10.1039/c8py01734d.

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42

Yang, Seungdo, Soyeon Jeong, Chunghyeon Ban, Hyungjoo Kim, and Do Heui Kim. "Catalytic Cleavage of Ether Bond in a Lignin Model Compound over Carbon-Supported Noble Metal Catalysts in Supercritical Ethanol." Catalysts 9, no. 2 (February 6, 2019): 158. http://dx.doi.org/10.3390/catal9020158.

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Decomposition of lignin-related model compound (benzyl phenyl ether, BPE) to phenol and toluene was performed over carbon-supported noble metal (Ru, Pd, and Pt) catalysts in supercritical ethanol without supply of hydrogen. Phenol and toluene as target products were produced by the hydrogenolysis of BPE. The conversion of BPE was higher than 95% over all carbon-supported noble metal catalysts at 270 ° for 4 h. The 5 wt% Pd/C demonstrated the highest yield (ca. 59.3%) of the target products and enhanced conversion rates and reactivity more significantly than other catalysts. In the case of Ru/C, BPE was significantly transformed to other unidentified byproducts, more so than other catalysts. The Pt/C catalyst produced the highest number of byproducts such as alkylated phenols and gas-phase products, indicating that the catalyst promotes secondary reactions during the decomposition of BPE. In addition, a model reaction using phenol as a reactant was conducted to check the secondary reactions of phenol such as alkylation or hydrogenation in supercritical ethanol. The product distribution when phenol was used as a reactant was mostly consistent with BPE as a reactant. Based on the results, plausible reaction pathways were proposed.

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43

Moreau, Claude, Jacques Joffre, Christian Saenz, Julio Carlos Afonso, and Jean-Louis Portefaix. "Mechanism of carbon sp2-heteroatom bond cleavage in hydroprocessing of substituted benzenes over unsupported transition metal sulfides." Journal of Molecular Catalysis A: Chemical 161, no. 1-2 (November 2000): 141–47. http://dx.doi.org/10.1016/s1381-1169(00)00315-0.

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44

Weber, Jaques, E. Peter Kundig, Annick Goursot, and Edouard Penigault. "The electronic structures of bis(η6-benzene)- and bis(η6-naphthalene)chromium(0)." Canadian Journal of Chemistry 63, no. 7 (July 1, 1985): 1734–40. http://dx.doi.org/10.1139/v85-291.

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SCF MS Xα molecular orbital calculations are reported for the bis(η6-benzene)- and bis(η6-naphthalene)chromium(0) complexes. The bonding may be essentially discussed in terms of the covalent interactions between the metal 3d and ligand π and π* orbitals. The different charges on chromium atom in the two systems are explained by the different balances between ligand-to-metal (bonding) and metal-to-ligand (back-bonding) electron donations. Some resemblances are found between the electronic structures of the two compounds and it is possible to correlate to a large extent the energy levels of their molecular orbitals. However, a shift towards lower values is predicted for the energy levels of the naphthalene complex, together with a large disruption of all the virtual π* and 3d* levels. This would undoubtedly favor nucleophilic attack followed by metal–ring or carbon–carbon bond cleavage, in agreement with the extreme lability of the coordinated arene rings observed in this complex.

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45

Hasegawa, Eietsu, Kazuma Mori, Shiori Tsuji, Kazuki Nemoto, Taku Ohta, and Hajime Iwamoto. "Visible Light-Promoted Metal-Free Reduction of Organohalides by 2-Naphthyl or 2-Hydroxynaphthyl-Substituted 1,3-Dimethylbenzimidazolines." Australian Journal of Chemistry 68, no. 11 (2015): 1648. http://dx.doi.org/10.1071/ch15396.

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The visible light-promoted reduction reactions of some organohalides were investigated using 2-aryl-1,3-dimethylbenzimidazolines (Ar-DMBIH) possessing 2-naphthyl or 2-hydroxynaphthyl substituents. In these reduction reactions, single-electron transfer from photo-excited Ar-DMBIH, attained by Xe lamp irradiation through an appropriate glass-filter (λ > 390 nm), to the halide substrates leads to the carbon–halogen bond cleavage, followed by the rearrangements of the formed carbon radicals such as 5-exo hexenyl cyclization and the Dowd–Beckwith ring expansion. Addition of 1,8-diazabicyclo[5.4.0]undec-7-ene was found to enhance the reducing ability of hydroxynaphthyl-substituted DMBIH. A household white light-emitting diode was also used as a light source for these reactions.

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46

Kondo, Teruyuki, and Take-aki Mitsudo. "ChemInform Abstract: Transition Metal Complex Catalyzed Selective Cleavage of Carbon-Carbon Bonds: A β-Carbon Elimination Reaction." ChemInform 32, no. 14 (April 3, 2001): no. http://dx.doi.org/10.1002/chin.200114296.

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47

FUKUZUMI, Shunichi, and Toshio TANAKA. "Cleavage and formation of metal-carbon .SIGMA. bonds associated with redox reactions." Journal of Synthetic Organic Chemistry, Japan 46, no. 7 (1988): 667–80. http://dx.doi.org/10.5059/yukigoseikyokaishi.46.667.

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48

Liu, Long, Yuanyuan Tang, Kunyu Wang, Tianzeng Huang, and Tieqiao Chen. "Transition-Metal-Free and Base-Promoted Carbon–Heteroatom Bond Formation via C–N Cleavage of Benzyl Ammonium Salts." Journal of Organic Chemistry 86, no. 5 (February 16, 2021): 4159–70. http://dx.doi.org/10.1021/acs.joc.0c02992.

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49

Yoshida, Hiroto, Takeshi Kishida, Masahiko Watanabe, and Joji Ohshita. "Fluorenes as new molecular scaffolds for carbon–carbon σ-bond cleavage reaction: acylfluorenylation of arynes." Chemical Communications, no. 45 (2008): 5963. http://dx.doi.org/10.1039/b814597k.

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50

Wang, Zhenhua, Xiu Wang, and Yasushi Nishihara. "Nickel-catalysed decarbonylative borylation of aroyl fluorides." Chemical Communications 54, no. 99 (2018): 13969–72. http://dx.doi.org/10.1039/c8cc08504h.

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A transformation of aroyl fluorides with diboron via nickel-catalysed carbon–fluorine bond cleavage and a sequential decarbonylation, which provides an efficient protocol to functionalize arylboronates, has been reported.

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