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Journal articles on the topic 'Cleavage of Carbon'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Zhou, Junhui, Xuan Qin, Shenzhi Zhou, Kevin R. MacKenzie, and Feng Li. "CYP3A-Mediated Carbon–Carbon Bond Cleavages in Drug Metabolism." Biomolecules 14, no. 9 (2024): 1125. http://dx.doi.org/10.3390/biom14091125.

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Cytochrome P450 enzymes (P450s) play a critical role in drug metabolism, with the CYP3A subfamily being responsible for the biotransformation of over 50% of marked drugs. While CYP3A enzymes are known for their extensive catalytic versatility, one intriguing and less understood function is the ability to mediate carbon–carbon (C–C) bond cleavage. These uncommon reactions can lead to unusual metabolites and potentially influence drug safety and efficacy. This review focuses on examining examples of C–C bond cleavage catalyzed by CYP3A, exploring the mechanisms, physiological significance, and i

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2

Liu, Hui, Minghao Feng, and Xuefeng Jiang. "Unstrained CarbonCarbon Bond Cleavage." Chemistry - An Asian Journal 9, no. 12 (2014): 3360–89. http://dx.doi.org/10.1002/asia.201402591.

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3

Amadio, Emanuele, Rosalia Di Lorenzo, Cristiano Zonta, and Giulia Licini. "Vanadium catalyzed aerobic carbon–carbon cleavage." Coordination Chemistry Reviews 301-302 (October 2015): 147–62. http://dx.doi.org/10.1016/j.ccr.2015.06.004.

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4

Perrott, A. L., H. J. P. De Lijser та D. R. Arnold. "The importance of conformational effects on the carbon–carbon bond cleavage of β-phenethyl ether radical cations". Canadian Journal of Chemistry 75, № 4 (1997): 384–97. http://dx.doi.org/10.1139/v97-044.

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The photosensitized (electron transfer) bond cleavage of some β-phenylethyl ether radical cations has been investigated. In previous studies the feasibility of the bond cleavage was thought to depend on the bond dissociation energy (BDE). However, this simple hypothesis led to several incorrect predictions and therefore additional criteria, conformational effects, were added to the hypothesis. This study has now been extended and additional examples of the importance of the conformation on the carbon–carbon bond cleavage of radical cations are provided. The four β-phenylethyl ethers studied ar

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5

Arnold, Donald R., and Laurie J. Lamont. "Photosensitized (electron transfer) carbon–carbon bond cleavage of radical cations: the 2-phenylethyl ether and acetal systems." Canadian Journal of Chemistry 67, no. 12 (1989): 2119–27. http://dx.doi.org/10.1139/v89-330.

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The scope of the photosensitized (electron transfer) carbon–carbon bond cleavage involving radical cations has been defined for 2-phenylethyl ethers and acetals. The thresholds for reactivity of the monophenylethyl and gem-diphenylethyl derivatives are compared. While the radical cation of methyl 2,2-diphenylethyl ether (7) cleaves to give ultimately diphenylmethane (2) and dimethoxymethane (8), the radical cation of methyl 2-phenylethyl ether (9) was stable under these conditions. In contrast to the lack of reactivity of the radical cation of 9, the radical cations of methyl 2-phenyl-2-propyl

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6

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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7

Allpress, Caleb J., and Lisa M. Berreau. "Oxidative aliphatic carbon–carbon bond cleavage reactions." Coordination Chemistry Reviews 257, no. 21-22 (2013): 3005–29. http://dx.doi.org/10.1016/j.ccr.2013.06.001.

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8

Liu, Hui, Minghao Feng, and Xuefeng Jiang. "ChemInform Abstract: Unstrained Carbon-Carbon Bond Cleavage." ChemInform 46, no. 36 (2015): no. http://dx.doi.org/10.1002/chin.201536277.

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9

van Maarseveen, Jan H. "Solid Phase Synthesis of Heterocycles by Cyclization/Cleavage Methodologiest." Combinatorial Chemistry & High Throughput Screening 1, no. 4 (1997): 185–214. http://dx.doi.org/10.2174/1386207301666220125213031.

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For the solid phase preparation of various (pharmacologically important) heterocycles, cyclization/cleavage (C/C) or cyclorelease strategies proved to be superior. CC approaches take utmost advantage of the benefits of sol)d phase synthesis. Besides the practical benefits of solid phase reactions, cyclative release approaches are distinguished especially because of the generally found high purity of the final detached products, since only the anticipated structures cleave off the resin. Also cyclization/cleavage strategies are "traceless", as the obtained moiety after cyclization is part of th

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10

T., S. S. Rao, and Awasthi Shubhra. "Oxidative cleavage of carbon-carbon triple bond - a-review." Journal of Indian Chemical Society Vol. 80, Dec 2003 (2003): 1129–41. https://doi.org/10.5281/zenodo.5839811.

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Department of Chemistry, Dr. H. S. Gour Yishwavidyalaya, Sagar-470 003, India E-mail : drtssrao@yahoo.co.in <em>Manuscript received 20 October 2003</em> Oxidation of phenylacetylene with molecular· oxygen led to the formation of 10 oxygen containing products along with dimerisation, oligomcrisation and polymerisation products. Benzaldehyde, benzoic acid and benzoic anhydride are the main oxidation products. The autoxidation of diphenylacetylene gives benzil as the main product and its yield increases upon use of ditertiary-butylperox1de as initiator. Examination of the erode oxidation m

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11

Sivaguru, Paramasivam, Zikun Wang, Giuseppe Zanoni, and Xihe Bi. "Cleavage of carbon–carbon bonds by radical reactions." Chemical Society Reviews 48, no. 9 (2019): 2615–56. http://dx.doi.org/10.1039/c8cs00386f.

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12

SANJAY, TALUKDAR, and BANERJI ASOKE. "Design and Development of New Chemical Reactions via Low-valent Titanium induced Cleavage of Carbon - Heteroatom Bonds." Journal of Indian Chemical Society Vol. 74, Nov-Dec 1997 (1997): 842–47. https://doi.org/10.5281/zenodo.5900308.

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Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai-400 085 <em>Manuscript received 13 August 1997</em> Low-valent titanium (LVT)-induced regioselective cleavage of <em>N</em>-aryl methyl bonds in preference to <em>N</em>-alkyl/aryl counterparts in N-arylmethylamines has been examined in detail and culminated in the design and development of new reactions, viz. novel approach to deprotection of <em>N</em>-benzylamines, reductive deoxygenation of carbonyls to methylenes and reductive amination of carbonyls under neutral conditions-all involving a known bonding change, viz. the directed

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13

Marek, Ilan. "Introduction: Carbon-Carbon Bond Cleavage in Stereoselective Synthesis." Chemical Reviews 121, no. 1 (2021): 1–2. http://dx.doi.org/10.1021/acs.chemrev.0c01216.

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14

Miyamoto, Kazunori, and Masahito Ochiai. "Organocatalytic Oxidative Cleavage of Carbon-Carbon Double Bonds." Journal of Synthetic Organic Chemistry, Japan 68, no. 3 (2010): 228–37. http://dx.doi.org/10.5059/yukigoseikyokaishi.68.228.

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15

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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16

Maslak, Przemyslaw, and Jozef Kula. "Carbon-Carbon Bond Cleavage in Photogenerated Radical Anions." Molecular Crystals and Liquid Crystals 194, no. 1 (1991): 293–304. http://dx.doi.org/10.1080/00268949108041179.

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17

Xu, Bao‐Hua, Gerald Kehr, Roland Fröhlich, and Gerhard Erker. "Carbon–Carbon Bond Cleavage by Strongly Electrophilic Boranes." Chemistry – A European Journal 16, no. 42 (2010): 12538–40. http://dx.doi.org/10.1002/chem.201002047.

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18

Amadio, Emanuele, Rosalia Di Lorenzo, Cristiano Zonta, and Giulia Licini. "ChemInform Abstract: Vanadium Catalyzed Aerobic Carbon-Carbon Cleavage." ChemInform 46, no. 45 (2015): no. http://dx.doi.org/10.1002/chin.201545261.

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19

Luo, Zhicheng, Chong Liu, Alexandra Radu, et al. "Carbon–carbon bond cleavage for a lignin refinery." Nature Chemical Engineering 1, no. 1 (2024): 61–72. http://dx.doi.org/10.1038/s44286-023-00006-0.

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20

Carrión, Ornella, Chun-Yang Li, Ming Peng, et al. "DMSOP-cleaving enzymes are diverse and widely distributed in marine microorganisms." Nature Microbiology 8, no. 12 (2023): 2326–37. http://dx.doi.org/10.1038/s41564-023-01526-4.

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AbstractDimethylsulfoxonium propionate (DMSOP) is a recently identified and abundant marine organosulfur compound with roles in oxidative stress protection, global carbon and sulfur cycling and, as shown here, potentially in osmotolerance. Microbial DMSOP cleavage yields dimethyl sulfoxide, a ubiquitous marine metabolite, and acrylate, but the enzymes responsible, and their environmental importance, were unknown. Here we report DMSOP cleavage mechanisms in diverse heterotrophic bacteria, fungi and phototrophic algae not previously known to have this activity, and highlight the unappreciated im

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21

Shao, Ailong, Meng Gao, Songtao Chen, Tao Wang, and Aiwen Lei. "CO/O2 assisted oxidative carbon–carbon and carbon–heteroatom bond cleavage for the synthesis of oxosulfonates from DMSO and olefins." Chemical Science 8, no. 3 (2017): 2175–78. http://dx.doi.org/10.1039/c6sc04480h.

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22

Kochergin, V. K., R. A. Manzhos, N. S. Komarova, et al. "Features of the Synthesis of Few-Layer Phosphorene Structures During Plasma Electrochemical Cleavage of Black Phosphorus." Himiâ vysokih ènergij 58, no. 3 (2024): 216–20. http://dx.doi.org/10.31857/s0023119324030069.

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A comparative study of the emission spectra of cathode electrolysis plasma during plasma electrochemical cleavage of black phosphorus and graphite under maximally identical experimental conditions has been carried out. A significantly lower concentration of active intermediates (OH radicals and O atoms) in the electrolysis plasma during the cleavafe of black phosphorus was found compared with a graphite electrode. It is assumed that this effect is due to a significantly higher rate of interaction of these intermediates with synthesized phosphorene structures than with graphene-like particles.

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23

Deke, Shi, Liu Jun Hai, and Cheng Yao Qiang. "Cleavage fracture in high carbon bainite." Materials Science and Engineering: A 158, no. 1 (1992): 11–19. http://dx.doi.org/10.1016/0921-5093(92)90130-s.

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24

Maslak, Przemyslaw, Jozef Kula, and Javier N. Narvaez. "Carbon-carbon bond cleavage by the dianion mechanism. Small kinetic advantage over the radical anion cleavage." Journal of Organic Chemistry 55, no. 8 (1990): 2277–79. http://dx.doi.org/10.1021/jo00295a006.

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25

Roque, Jose B., Yusuke Kuroda, Lucas T. Göttemann, and Richmond Sarpong. "Deconstructive fluorination of cyclic amines by carbon-carbon cleavage." Science 361, no. 6398 (2018): 171–74. http://dx.doi.org/10.1126/science.aat6365.

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26

Schaub, Thomas, Christian Döring, and Udo Radius. "Efficient nickel mediated carbon–carbon bond cleavage of organonitriles." Dalton Trans., no. 20 (2007): 1993–2002. http://dx.doi.org/10.1039/b702959d.

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27

Crabtree, Robert H., Robert P. Dion, David J. Gibboni, Dominic V. McGrath, and Elizabeth M. Holt. "Carbon-carbon bond cleavage in hydrocarbons by iridium complexes." Journal of the American Chemical Society 108, no. 23 (1986): 7222–27. http://dx.doi.org/10.1021/ja00283a015.

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28

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

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29

Hilvert, Donald. "Antibody catalysis of carbon-carbon bond formation and cleavage." Accounts of Chemical Research 26, no. 10 (1993): 552–58. http://dx.doi.org/10.1021/ar00034a006.

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30

Deng, Ruixian, Junwei Xi, Qigang Li, and Zhenhua Gu. "Enantioselective Carbon-Carbon Bond Cleavage for Biaryl Atropisomers Synthesis." Chem 5, no. 7 (2019): 1834–46. http://dx.doi.org/10.1016/j.chempr.2019.04.008.

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31

Takahashi, Tamotsu, Martin Kotora, Ryuichiro Hara, and Zhenfeng Xi. "Carbon–Carbon Bond Cleavage and Selective Transformation of Zirconacycles." Bulletin of the Chemical Society of Japan 72, no. 12 (1999): 2591–602. http://dx.doi.org/10.1246/bcsj.72.2591.

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32

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

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33

Murai, Masahito, Atsushi Nishiyama, Naoki Nishinaka, Haruka Morita, and Kazuhiko Takai. "Iridium-catalysed hydrosilylation of cyclopropanes via regioselective carbon–carbon bond cleavage." Chemical Communications 53, no. 66 (2017): 9281–84. http://dx.doi.org/10.1039/c7cc04296e.

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34

Cheng, Zengrui, Kaimeng Huang, Chen Wang, et al. "Catalytic remodeling of complex alkenes to oxonitriles through C=C double bond deconstruction." Science 387, no. 6738 (2025): 1083–90. https://doi.org/10.1126/science.adq8918.

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Deconstructive transformation of carbon-carbon double bonds (C=C) is a pivotal strategy in synthetic chemistry and drug discovery. Despite the substantial advances in olefin metathesis and ozonolysis for natural product synthesis through C=C double-bond cleavage, the catalytic remodeling of complex molecules through C=C double-bond deconstruction has been underdeveloped. We report a heterogeneous copper-catalyzed C=C double-bond cleavage, which enables the remodeling of complex molecules by converting the carbons on either side of the C=C double bond to carbonyl and cyano groups, respectively.

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35

Liu, Can, Xianjin Zhu, Yongzhen Han, Haijun Yang, Changjin Zhu, and Hua Fu. "Superbase-promoted selective carbon–carbon bond cleavage driven by aromatization." Organic & Biomolecular Chemistry 17, no. 20 (2019): 4984–89. http://dx.doi.org/10.1039/c9ob00606k.

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A novel selective carbon–carbon single bond cleavage has been disclosed through the copper-catalyzed reaction of 1-alkyl-3-alkylindolin-2-imine hydrochlorides with substituted 1-(bromomethyl)-2-iodobenzenes leading to fused N-heterocycles.

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36

Itoh, Akichika, Tomoaki Yamaguchi, Tomoya Nobuta, et al. "Catalytic Aerobic Photooxidative Cleavage of Carbon-Carbon Triple Bonds Using Carbon Tetrabromide." Synlett 24, no. 05 (2013): 607–10. http://dx.doi.org/10.1055/s-0032-1318308.

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37

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

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38

Wu, Kong, Chan Song, and Dongmei Cui. "Advances of Unstrained Carbon-Carbon Single Bond Cleavage with Oxygen." Chinese Journal of Organic Chemistry 37, no. 3 (2017): 586. http://dx.doi.org/10.6023/cjoc201609030.

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39

Cicchillo, Robert M., Houjin Zhang, Joshua A. V. Blodgett, et al. "An unusual carbon–carbon bond cleavage reaction during phosphinothricin biosynthesis." Nature 459, no. 7248 (2009): 871–74. http://dx.doi.org/10.1038/nature07972.

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40

Al-Mestarihi, Ahmad, Anthony Romo, Hung-wen Liu, and Brian O. Bachmann. "Nitrososynthase-Triggered Oxidative Carbon–Carbon Bond Cleavage in Baumycin Biosynthesis." Journal of the American Chemical Society 135, no. 31 (2013): 11457–60. http://dx.doi.org/10.1021/ja404987r.

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41

Zhou, Jingwei, Ruibo Wu, Binju Wang, Zexing Cao, Honggao Yan, and Yirong Mo. "Proton-Shuttle-Assisted Heterolytic Carbon–Carbon Bond Cleavage and Formation." ACS Catalysis 5, no. 5 (2015): 2805–13. http://dx.doi.org/10.1021/acscatal.5b00079.

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42

Maslak, Przemyslaw, and Stacey L. Asel. "ESR investigation of carbon-carbon bond cleavage in radical cations." Journal of the American Chemical Society 110, no. 24 (1988): 8260–61. http://dx.doi.org/10.1021/ja00232a062.

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43

Kamimura, Akio, Kosuke Ikeda, Takaaki Moriyama, and Hidemitsu Uno. "Unexpected reductive double carbon–carbon bonds cleavage of bicyclic nitrocyclopropanes." Tetrahedron Letters 54, no. 14 (2013): 1842–44. http://dx.doi.org/10.1016/j.tetlet.2013.01.094.

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44

Okamoto, Akio, Miles S. Snow, and Donald R. Arnold. "Photosensitized (electron transfer) carbon-carbon bond cleavage of radical cations." Tetrahedron 42, no. 22 (1986): 6175–87. http://dx.doi.org/10.1016/s0040-4020(01)88078-9.

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45

Basheer, Ahmad, Masaaki Mishima, and Ilan Marek. "Regioselective Carbon–Carbon Bond Cleavage in the Oxidation of Cyclopropenylcarbinols." Organic Letters 13, no. 15 (2011): 4076–79. http://dx.doi.org/10.1021/ol201581c.

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46

Bockman, T. Michael, Stephan M. Hubig, and Jay K. Kochi. "Direct Observation of Carbon−Carbon Bond Cleavage in Ultrafast Decarboxylations." Journal of the American Chemical Society 118, no. 18 (1996): 4502–3. http://dx.doi.org/10.1021/ja960112j.

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47

Varfaj, Fatbardha, Siti N. A. Zulkifli, Hyoung-Goo Park, Victoria L. Challinor, James J. De Voss, and Paul R. Ortiz de Montellano. "Carbon-Carbon Bond Cleavage in Activation of the Prodrug Nabumetone." Drug Metabolism and Disposition 42, no. 5 (2014): 828–38. http://dx.doi.org/10.1124/dmd.114.056903.

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48

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

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49

Dangi, Bikash, and Tae‐Jin Oh. "Bacterial CYP 154C8 catalyzes carbon‐carbon bond cleavage in steroids." FEBS Letters 593, no. 1 (2018): 67–79. http://dx.doi.org/10.1002/1873-3468.13297.

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50

Miyamoto, Kazunori, and Masahito Ochiai. "ChemInform Abstract: Organocatalytic Oxidative Cleavage of Carbon-Carbon Double Bonds." ChemInform 41, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.201033237.

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