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Journal articles on the topic 'N–H bond cleavage'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Guo, Qihang, and Zhan Lu. "Recent Advances in Nitrogen–Nitrogen Bond Formation." Synthesis 49, no. 17 (August 7, 2017): 3835–47. http://dx.doi.org/10.1055/s-0036-1588512.

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Over the last decade, N–N bond formation as a synthetic strategy has emerged as a powerful key step in the construction of highly valuable heterocycles from easily obtained materials. This review focuses on recent methods used to build N–N bonds, classified by intra- and intermolecular reactions with various types of N–X (O, C, N, H) bond cleavage.1 I ntroduction2 Intramolecular N–N Bond Formation2.1 Cleavage of N–O Bonds2.2 Cleavage of N–C Bonds2.3 Cleavage of N–N Bonds2.4 Cleavage of N–H Bonds2.4.1 Construction of Pyrazole Derivatives2.4.2 Construction of Triazole Derivatives2.4.3 Construction of Indazole and Pyrazoline Derivatives2.4.4 Construction of Other N–N Bond Derivatives3 Intermolecular N–N Bond Formation4 Conclusion

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2

Wang, Zhong-Xia, and Bo Yang. "Chemical transformations of quaternary ammonium salts via C–N bond cleavage." Organic & Biomolecular Chemistry 18, no. 6 (2020): 1057–72. http://dx.doi.org/10.1039/c9ob02667c.

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3

Yu, Yang, Gen Luo, Jimin Yang, and Yi Luo. "Theoretical studies on the N–X (X = Cl, O) bond activation mechanism in catalytic C–H amination." Catalysis Science & Technology 10, no. 6 (2020): 1914–24. http://dx.doi.org/10.1039/c9cy02555c.

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A favorable S_N2-type N–Cl bond cleavage mechanism are proposed for Rh-catalysed C–H amination, which also works for N–O bond cleavage in Rh, Ru, and Pd analogous systems. These results could provide new understanding of C–H amination.

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4

Feng, Simin, Shan Li, Jing Li, and Junfa Wei. "Palladium-catalyzed annulation of N-alkoxy benzsulfonamides with arynes by C–H functionalization: access to dibenzosultams." Organic Chemistry Frontiers 6, no. 4 (2019): 517–22. http://dx.doi.org/10.1039/c8qo01311j.

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5

Tnay, Ya Lin, Gim Yean Ang, and Shunsuke Chiba. "Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines." Beilstein Journal of Organic Chemistry 11 (October 19, 2015): 1933–43. http://dx.doi.org/10.3762/bjoc.11.209.

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We report herein studies on copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines. Treatment of N–H ketimines having an α-sp3 hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C–C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for the construction of oxaspirocyclohexadienones as well as in the electrophilic cyanation of Grignard reagents with pivalonitrile as a CN source.

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6

Suzuki, Hiroharu, Akiko Inagaki, Kouki Matsubara, and Toshifumi Takemori. "Alkane activation on a multimetallic site." Pure and Applied Chemistry 73, no. 2 (January 1, 2001): 315–18. http://dx.doi.org/10.1351/pac200173020315.

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Trinuclear polyhydrido complex of ruthenium effectively activates alkanes to cleave C-H bonds in a selective manner due to cooperative action of the metal centers. The reaction of (Cp´Ru) 3 (m-H) 3 (m3 -H) 2 (1) (Cp´ = h5-C5Me5) with n-alkane at 170 °C leads to the formation of a trinuclear closo-ruthenacyclopentadiene complex as a result of a successive cleavage of six C-H bonds. Introduction of a m3-sulfido ligand into the Ru3 core of the trirutheniumpolyhydrido cluster significantly modifies the regioselectivity of the alkane C-H activation. Heating of a solution of (Cp´Ru) 3 (m3-S) (m-H) 3 (4) in alkane exclusively gives a trinuclear m3-alkylidyne complex via a selective C-H bond cleavage at the less-hindered terminus of alkane molecule.

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7

GuhaRoy, Chhandasi, Ray J. Butcher, and Samaresh Bhattacharya. "Rhodium complexes of 1,3-diaryltriazenes: Usual coordination, N–H bond activation and, N–N and C–N bond cleavage." Journal of Organometallic Chemistry 693, no. 26 (December 2008): 3923–31. http://dx.doi.org/10.1016/j.jorganchem.2008.10.006.

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8

Zhou, Xueer, Petra Vasko, Jamie Hicks, M. Ángeles Fuentes, Andreas Heilmann, Eugene L. Kolychev, and Simon Aldridge. "Cooperative N–H bond activation by amido-Ge(ii) cations." Dalton Transactions 49, no. 27 (2020): 9495–504. http://dx.doi.org/10.1039/d0dt01960g.

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Germylium-ylidene cations, [R(L)Ge]⁺, featuring amido substituents at R and NHC or phosphine donors at L have been synthesized and structurally characterized. The Lewis acidic germanium cation and proximal amide function allow for facile cleavage of N–H bonds in 1,2 fashion.

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9

Wang, Xiaoping, Tianbiao Liu, R. Morris Bullock, and Christina Hoffmann. "Heterolytic Cleavage of H2 Revealed by Neutron Single Crystal Diffraction." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C922. http://dx.doi.org/10.1107/s2053273314090779.

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Synthetic biologically inspired complexes exhibiting reactivity similar to hydrogenase enzymes have provided evidence of hydride transfer to the metal and proton transfer to an amine, but key structural information about the intermediate is not readily discernible with X-rays. The greater sensitivity of neutron to hydrogen makes it ideal for studying the structure and dynamics of catalytic materials. The newly commissioned TOPAZ neutron single crystal diffractometer at the SNS is capable of continuous 3D diffraction space mapping from a small stationary crystal, permitting detailed structural study at atomic resolution. The structure measured on TOPAZ for an Fe-based mononuclear electrocatalyst confirms that reaction of [CpFeN-L)](BARF) (1) with H2 under mild conditions leads to heterolytic cleavage of the H-H bond into a proton and hydride[1]. The precise location of H atoms in [Fe-H···H-N]+ reveals an unconventional H-bonding interaction, where the ferrous hydridic site {Fe(II)-H-} acts as the H-bond acceptor and the nitrogen of the protic pendant amine {L-N-H+} as the H-bond donor. The neutron structure provides clear evidence of a crucial intermediate involving an Fe-H···H-N interaction in the oxidation of H2. The result clarifies the key role of the pendant amine in the iron complex and provides insights into the design of synthetic electrocatalysts sought as cost-effective alternatives to platinum in fuel cells. The reaction is also a critical step in homogeneous catalysts for hydrogenation of C=O and C=N bonds. A preliminary result from TOPAZ measurement shows that 1 undergoes further single-crystal to single-crystal chemical reaction with moisture in the air, leading to a Fe(H2O)+ complex. Abbreviations: Cp = pentafluoropyridylcyclopentadienide; N-L= 1, 5-di(tert-butyl)-3,7-di(benzyl)-1,5-diaza-3,7-diphospha-cyclooctane; BARF = [B[3,5-(CF3)2C6H3]4]–

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10

KOELLIKER, R., and D. MILSTEIN. "ChemInform Abstract: Easy Cleavage of the N-H Bond of Ammonia." ChemInform 22, no. 33 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199133244.

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11

Vagánek, Adam, Ján Rimarčík, Michal Ilčin, Peter Škorňa, Vladimír Lukeš, and Erik Klein. "Homolytic N–H bond cleavage in anilines: Energetics and substituent effect." Computational and Theoretical Chemistry 1014 (June 2013): 60–67. http://dx.doi.org/10.1016/j.comptc.2013.03.027.

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12

Wu, R. R., and M. T. Rodgers. "Mechanisms and energetics for N-glycosidic bond cleavage of protonated adenine nucleosides: N3 protonation induces base rotation and enhances N-glycosidic bond stability." Physical Chemistry Chemical Physics 18, no. 23 (2016): 16021–32. http://dx.doi.org/10.1039/c6cp01445c.

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N3 protonation induces base rotation and stabilizes the syn orientation of the adenine nucleobase of [dAdo+H]⁺ and [Ado+H]⁺via formation of a strong intramolecular N3H⁺⋯O5′ hydrogen-bonding interaction, which in turn influences the mechanisms and energetics for N-glycosidic bond cleavage.

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13

Wu, Weirong, Yuxia Liu, and Siwei Bi. "Mechanistic insight into conjugated N–N bond cleavage by Rh(iii)-catalyzed redox-neutral C–H activation of pyrazolones." Organic & Biomolecular Chemistry 13, no. 30 (2015): 8251–60. http://dx.doi.org/10.1039/c5ob00977d.

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14

Wu, R. R., and M. T. Rodgers. "Tautomerization lowers the activation barriers for N-glycosidic bond cleavage of protonated uridine and 2′-deoxyuridine." Physical Chemistry Chemical Physics 18, no. 35 (2016): 24451–59. http://dx.doi.org/10.1039/c6cp03620a.

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15

Harrison, Alex G. "Structural and sequence effects in the fragmentation of protonated tripeptides containing tyrosine." Canadian Journal of Chemistry 83, no. 11 (November 1, 2005): 1969–77. http://dx.doi.org/10.1139/v05-206.

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The fragmentation reactions of a variety of protonated tripeptides containing tyrosine in the three possible positions have been studied by energy-resolved collision-induced dissociation mass spectrometry. The primary fragmentation reactions involve cleavage of the N-terminal and (or) C-terminal amide bond with the relative importance of the two cleavages depending strongly on the identity and position of the amino acid residues in the tripeptide. The results are interpreted in terms of the a1y mechanism for cleavage of the N-terminal amide bond and the bxyz mechanism for cleavage of the C-terminal amide bond and, indeed, provide support for these mechanisms. However, it appears likely that, for protonated H-Val-Tyr-Pro-OH, the neutral accompanying formation of the y1 (protonated proline) ion is a cyclic dipeptide (cyclo-Val-Tyr) rather than the oxazolone predicted by the bxyz mechanism.Key words: tyrosine-containing peptides, fragmentation mechanisms, tandem mass spectrometry.

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16

Zhao, Huai-Bo, Zhong-Wei Hou, Zhan-Jiang Liu, Ze-Feng Zhou, Jinshuai Song, and Hai-Chao Xu. "Amidinyl Radical Formation through Anodic N−H Bond Cleavage and Its Application in Aromatic C−H Bond Functionalization." Angewandte Chemie 129, no. 2 (December 9, 2016): 602–5. http://dx.doi.org/10.1002/ange.201610715.

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17

Zhao, Huai-Bo, Zhong-Wei Hou, Zhan-Jiang Liu, Ze-Feng Zhou, Jinshuai Song, and Hai-Chao Xu. "Amidinyl Radical Formation through Anodic N−H Bond Cleavage and Its Application in Aromatic C−H Bond Functionalization." Angewandte Chemie International Edition 56, no. 2 (December 9, 2016): 587–90. http://dx.doi.org/10.1002/anie.201610715.

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18

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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19

Terasawa, Jyunichi, Yu Shibata, Miho Fukui, and Ken Tanaka. "[2+2+2] Annulation of N-(1-Naphthyl)acetamide with Two Alkynoates via Cleavage of Adjacent C–H and C–N Bonds Catalyzed by an Electron-Deficient Rhodium(III) Complex." Molecules 23, no. 12 (December 14, 2018): 3325. http://dx.doi.org/10.3390/molecules23123325.

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It has been established that an electron-deficient cationic CpE-rhodium(III) complex catalyzes the non-oxidative [2+2+2] annulation of N-(1-naphthyl)acetamide with two alkynoates via cleavage of the adjacent C–H and C–N bonds to give densely substituted phenanthrenes under mild conditions (at 40 °C under air). In this reaction, a dearomatized spiro compound was isolated, which may support the formation of a cationic spiro rhodacycle intermediate in the catalytic cycle. The use of N-(1-naphthyl)acetamide in place of acetanilide switched the reaction pathway from the oxidative [2+2+2] annulation-lactamization via C–H/C–H cleavage to the non-oxidative [2+2+2] annulation via C–H/C–N cleavage. This chemoselectivity switch may arise from stabilization of the carbocation in the above cationic spiro rhodacycle by the neighboring phenyl and acetylamino groups, resulting in the nucleophilic C–C bond formation followed by β-nitrogen elimination.

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20

He, Kaixuan, Pengfei Li, Shuwei Zhang, Qian Chen, Honghe Ji, Yu Yuan, and Xiaodong Jia. "One-step construction of molecular complexity by tert-butyl nitrite (TBN)-initiated cascade α,β-sp3 C–H bond difunctionalization and C–N bond cleavage." Chemical Communications 54, no. 94 (2018): 13232–35. http://dx.doi.org/10.1039/c8cc06946h.

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21

Tayebani, Maryam, Sandro Gambarotta, and Glenn Yap. "C−H versus C−N Bond Cleavage Promoted by Niobium(II) Amide." Organometallics 17, no. 17 (August 1998): 3639–41. http://dx.doi.org/10.1021/om980298q.

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22

Brückner, Tobias, Merle Arrowsmith, Merlin Heß, Kai Hammond, Marcel Müller, and Holger Braunschweig. "Synthesis of fused B,N-heterocycles by alkyne cleavage, NHC ring-expansion and C–H activation at a diboryne." Chemical Communications 55, no. 47 (2019): 6700–6703. http://dx.doi.org/10.1039/c9cc02657f.

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The addition of alkynes to a saturated N-heterocyclic carbene (NHC)-supported diboryne results in spontaneous cycloaddition, with complete BB and CC triple bond cleavage, NHC ring-expansion and activation of a variety of C–H bonds, leading to the formation of complex mixtures of fused B,N-heterocycles.

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23

Zhu, Longzhi, Xin Cao, Renhua Qiu, Takanori Iwasaki, Vutukuri Prakash Reddy, Xinhua Xu, Shuang-Feng Yin, and Nobuaki Kambe. "Copper-mediated thiolation of carbazole derivatives and related N-heterocycle compounds." RSC Advances 5, no. 49 (2015): 39358–65. http://dx.doi.org/10.1039/c5ra04965b.

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Cu-mediated direct thiolation of carbazole derivatives with disulfides via C–H bond cleavage to give diaryl and alkyl aryl sulfides which easily extends to the synthesis of thioethers with a benzo[h]quinolone, 2-phenylquinoline or indole moiety in satisfactory yields.

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24

Wu, Yingtao, Chao Pi, Yangjie Wu, and Xiuling Cui. "Directing group migration strategy in transition-metal-catalysed direct C–H functionalization." Chemical Society Reviews 50, no. 6 (2021): 3677–89. http://dx.doi.org/10.1039/d0cs00966k.

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In this tutorial review, the rapid advances of directing group (DG) migration in transition-metal-catalysed direct C–H activation was presented through analyzing and comparing the different bond cleavage trigger DG migration (including N–O, N–C, N–N or O–C).

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25

Milsmann, Carsten, Scott P. Semproni, and Paul J. Chirik. "N–N Bond Cleavage of 1,2-Diarylhydrazines and N–H Bond Formation via H-Atom Transfer in Vanadium Complexes Supported by a Redox-Active Ligand." Journal of the American Chemical Society 136, no. 34 (August 12, 2014): 12099–107. http://dx.doi.org/10.1021/ja5062196.

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26

Song, Liangliang, Xiaoyong Zhang, Xiao Tang, Luc Van Meervelt, Johan Van der Eycken, Jeremy N. Harvey, and Erik V. Van der Eycken. "Ruthenium-catalyzed cascade C–H activation/annulation of N-alkoxybenzamides: reaction development and mechanistic insight." Chemical Science 11, no. 42 (2020): 11562–69. http://dx.doi.org/10.1039/d0sc04434b.

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27

LIU, MIN HSIEN, and GEN FA ZHENG. "COMPUTATIONAL STUDY OF UNIMOLECULAR DECOMPOSITION MECHANISM OF RDX EXPLOSIVE." Journal of Theoretical and Computational Chemistry 06, no. 02 (June 2007): 341–51. http://dx.doi.org/10.1142/s0219633607002952.

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This study investigated the RDX (1,3,5-Trinitro-1,3,5-triazine) molecule to elucidate its possible decomposition species and the corresponding energies by performing the density-functional theory (DFT) calculations. Reasonable decomposition mechanisms are proposed based on the bond energy calculated using the differential overlap (INDO) program, which yields the weakest bonding site for reference and determines the site of easy cleavage. Computational results indicate that the activation energy of direct cis-form HONO elimination is lower than that of direct trans-form HONO elimination and that of a two-stage elimination of two forms of HONO ( N – N bond fission combined with C – H bond breaking) in the initial decomposition step, which are 213.9 kJ/mol and 93.8–101.8 kJ/mol, respectively. Two possible pathways are proposed; (1) N – N bond homolytic cleavage followed by elimination of cis-form HONO, and (2) N – N bond homolytic cleavage followed by elimination of trans-form HONO.

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28

Cohen, Revital, Boris Rybtchinski, Mark Gandelman, Linda J. W. Shimon, Jan M. L. Martin, and David Milstein. "Novel Azine Reactivity: Facile NN Bond Cleavage, CH Activation, and NN Coupling Mediated by RhI." Angewandte Chemie International Edition 42, no. 17 (April 29, 2003): 1949–52. http://dx.doi.org/10.1002/anie.200250571.

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29

Furukawa, Takayuki, Mamoru Tobisu, and Naoto Chatani. "Nickel-catalyzed borylation of arenes and indoles via C–H bond cleavage." Chemical Communications 51, no. 30 (2015): 6508–11. http://dx.doi.org/10.1039/c5cc01378j.

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The first nickel-catalyzed method for the borylation of carbon–hydrogen bonds in arenes and indoles is described. The use of an N-heterocyclic carbene ligand is essential for an efficient reaction, with an N-cyclohexyl-substituted derivative being optimal. This method is readily applied to the gram scale synthesis of 2-borylindole.

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30

Wu, R. R., Yu Chen, and M. T. Rodgers. "Mechanisms and energetics for N-glycosidic bond cleavage of protonated 2′-deoxyguanosine and guanosine." Physical Chemistry Chemical Physics 18, no. 4 (2016): 2968–80. http://dx.doi.org/10.1039/c5cp05738h.

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TCID thresholds of [dGuo/Guo+H]⁺ indicate that 2′-hydroxyl strengthens glycosidic bond stability but slightly weakens the competition between the two primary dissociation pathways of [Guo+H]⁺vs. [dGuo+H]⁺.

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31

Xia, Cheng-Cai, Ya-Fei Ji, Xiao-Pan Fu, Lu Chen, Gao-Rong Wu, and Hong-Wei Liu. "Cascade Access to Carboline Carboxylates from Indolyl Ketoximes and Acrylates via Palladium-Catalyzed C–H Bond Alkenylation/Annulation." Synlett 32, no. 01 (July 15, 2020): 69–74. http://dx.doi.org/10.1055/s-0040-1707192.

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An efficient palladium-catalyzed C–H bond alkenylation/annulation strategy to access carboline carboxylates from indolyl ketoximes and acrylates through C–C/C–N bond formation is reported. Indolyl ketoximes not only direct ortho-olefination with acrylates, but also undergo an intramolecular N–O bond cleavage/traceless annulation to construct carboline carboxylates straightforwardly in this concise method.

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32

Tennent, Christine L., and William D. Jones. "Kinetics and mechanism of dealkylation of coordinated isocyanide in Fe(PMe3)2(t-BuNC)3." Canadian Journal of Chemistry 83, no. 6-7 (June 1, 2005): 626–33. http://dx.doi.org/10.1139/v05-023.

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The zerovalent iron complex Fe(PMe3)2(t-BuNC)3 undergoes thermal cleavage of the CN bond to give Fe(PMe3)2(t-BuNC)2(H)(CN) and isobutylene. The reaction follows first order kinetics, and addition of the hydrogen-atom donor 1,4-cyclohexadiene leads to the preferential formation of isobutane rather than isobutylene. Mechanistic studies are consistent with a rate determining homolysis of the CN bond, giving rise to tert-butyl radicals.Key words: iron, isocyanide, elimination, CN cleavage.

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33

Lopes Jesus, A. J., Mário T. S. Rosado, R. Fausto, and I. Reva. "UV-induced radical formation and isomerization of 4-methoxyindole and 5-methoxyindole." Physical Chemistry Chemical Physics 22, no. 40 (2020): 22943–55. http://dx.doi.org/10.1039/d0cp04354k.

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34

Doddi, Adinarayana, Ganesan Prabusankar, Christian Gemel, Manuela Winter, and Roland A. Fischer. "N-Heterocyclic Gallylene Supported Organoruthenium Derivatives - Synthesis, Structure, and C-H Bond Cleavage." European Journal of Inorganic Chemistry 2013, no. 21 (June 12, 2013): 3609–15. http://dx.doi.org/10.1002/ejic.201300257.

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35

Lasri, Jamal, Naser Eltaher Eltayeb, Matti Haukka, and Bandar A. Babgi. "Crystal structure oftrans-dichloridobis[N-(5,5-dimethyl-4,5-dihydro-3H-pyrrol-2-yl-κN)acetamide]palladium(II) dihydrate." Acta Crystallographica Section E Crystallographic Communications 73, no. 4 (March 17, 2017): 528–30. http://dx.doi.org/10.1107/s2056989017003929.

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The title complex, [PdCl2(C8H14N2O)2]·2H2O, was obtained by N–O bond cleavage of the oxadiazoline rings of thetrans-[dichlorido-bis(2,5,5-trimethyl-5,6,7,7a-tetrahydropyrrolo[1,2-b][1,2,4]oxadiazole-N1)]palladium(II) complex. The palladium(II) atom exhibits an almost square-planar coordination provided by twotrans-arranged chloride anions and a nitrogen atom from each of the two neutral organic ligands. In the crystal, N—H...O, O—H...O and O—H...Cl hydrogen bonds link complex molecules into double layers parallel to thebcplane.

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36

Reid, Jonathan P., Richard A. Loomis, and Stephen R. Leone. "Competition between N−H and N−D Bond Cleavage in the Photodissociation of NH2D and ND2H†." Journal of Physical Chemistry A 104, no. 45 (November 2000): 10139–49. http://dx.doi.org/10.1021/jp001065r.

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37

Musat, Florin, Carsten Vogt, and Hans H. Richnow. "Carbon and Hydrogen Stable Isotope Fractionation Associated with the Aerobic and Anaerobic Degradation of Saturated and Alkylated Aromatic Hydrocarbons." Journal of Molecular Microbiology and Biotechnology 26, no. 1-3 (2016): 211–26. http://dx.doi.org/10.1159/000442161.

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Saturated hydrocarbons (alkanes) and alkylated aromatic hydrocarbons are abundant environmental compounds. Hydrocarbons are primarily removed from the environment by biodegradation, a process usually associated with moderate carbon and significant hydrogen isotope fractionation allowing monitoring of biodegradation processes in the environment. Here, we review the carbon and hydrogen stable isotope fractionation associated with the cleavage of C-H bonds at alkyl chains of hydrocarbons. Propane, <i>n</i>-butane and ethylbenzene were used as model components for alkyl moieties of aliphatic and aromatic hydrocarbons with emphasis on the cleavage of the C-H bond without the involvement of molecular oxygen. The carbon and hydrogen isotope fractionation factors were further used to explore the diagnostic potential for characterizing the mode of bond cleavage under oxic and anoxic conditions. Λ factors, calculated to correlate carbon and hydrogen fractionation, allowed to distinguish between aerobic and anaerobic biodegradation processes in the environment.

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38

MacKay, Bruce A., Samuel A. Johnson, Brian O. Patrick, and Michael D. Fryzuk. "Functionalization and cleavage of coordinated dinitrogen via hydroboration using primary and secondary boranes." Canadian Journal of Chemistry 83, no. 4 (April 1, 2005): 315–23. http://dx.doi.org/10.1139/v04-161.

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The reaction of the side-on, end-on ditantalum dinitrogen complex ([NPN]Ta)2(µ-η1:η2-N2)(µ-H)2 (where NPN = PhP(CH2SiMe2NPh)2) with a variety of secondary and primary boranes is reported. With 9-BBN, hydroboration of the Ta2N2 unit occurs via B-H addition, which in turn triggers a cascade of reactions that result in NN bond cleavage, ancillary ligand rearrangement involving silicon group migration, and finally elimination of benzene from the N-Ph group and a B-H moiety to generate the imidenitride derivative. In the presence of excess 9-BBN, the Lewis acid base adduct of the imidenitride ([NPµN]Ta(=NBC8H14)(µ-NB(H)C8H14)Ta[NPN]) is formed. A similar set of reactions is observed for dicyclohexylborane (Cy2BH), which hydroborates the dinitrogen complex to generate [NPN]Ta(H)(µ-η1:η2-NNBCy2)(µ-H)2Ta[NPN], followed by loss of H2 and silicon group migration to yield the imidenitride [NPµN]Ta(=NBCy2)(µ-N)(Ta[NPN]. With thexyl borane (H2BCMe2CHMe2), a similar sequence of reactions is suggested starting with hydroboration to generate [NPN]Ta(H)(µ-η1:η2-NNB(H)C6H13)(µ-H)2Ta[NPN], followed by loss of H2 and ancillary ligand rearrangement. When bis(pentafluorophenyl)borane (HB(C6F5)2) is used, no hydroboration of coordinated N2 is observed, rather simple adduct formation to give ([NPN]Ta)2(µ-η1:η2-NN-B(H)(C6F5)2)(µ-H)2 occurs. Key words: dinitrogen, tantalum, hydroboration, NN bond cleavage.

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39

Wang, Xia, Ya-Fei Han, Xuan-Hui Ouyang, Ren-Jie Song, and Jin-Heng Li. "The photoredox alkylarylation of styrenes with alkyl N-hydroxyphthalimide esters and arenes involving C–H functionalization." Chemical Communications 55, no. 97 (2019): 14637–40. http://dx.doi.org/10.1039/c9cc07494e.

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The In(OTf)₃-promoted three-component photoredox alkylarylation of styrenes with alkyl NHP esters and arenes to access alkylated arene derivatives through C–C bond cleavage and C–H functionalization is reported.

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40

You, Tingjie, Maosheng Zhang, Jianhui Chen, Hongmei Liu, and Yuanzhi Xia. "Ruthenium(ii)-catalyzed reductive N–O bond cleavage of N-OR (R = H, alkyl, or acyl) substituted amides and sulfonamides." Organic Chemistry Frontiers 8, no. 1 (2021): 112–19. http://dx.doi.org/10.1039/d0qo01093f.

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41

Wrackmeyer, Bernd, Gerald Kehr, and Saqib Alib. "Reaction of 9-Borabicyclo[3.3.1]nonane with N-Trimethylsilylamines – Cleavage of the N–Si or N–H Bond." Zeitschrift für Naturforschung B 53, no. 3 (March 1, 1998): 393–96. http://dx.doi.org/10.1515/znb-1998-0321.

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Abstract The reaction of dimeric 9-borabicyclo[3.3.1]no-nane 1 with N-trimethylsilyl-aniline 2 affords 9-anilino-9-borabicyclo[3.3.1]nonane 5 by elimination of trimethylsilane. In contrast, 1 reacts with the N-trimethylsilyl-2-aminopyridines 3 and 4 se lectively by elimination of H2 to give the corresponding N-trimethylsilyl-aminoboranes 6 and 7. The latter reactions proceed via formation of bo-rane-pyridine adducts.

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42

Driver, Michael S., and John F. Hartwig. "Energetics and Mechanism of Alkylamine N−H Bond Cleavage by Palladium Hydroxides: N−H Activation by Unusual Acid−Base Chemistry." Organometallics 16, no. 26 (December 1997): 5706–15. http://dx.doi.org/10.1021/om970856l.

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43

Shustorovich, Evgeny, and Alexis T. Bell. "Oxygen-assisted cleavage of OH, NH, and CH bonds on transition metal surfaces: bond-order-conservation-Morse-potential analysis." Surface Science 268, no. 1-3 (January 1992): 397–405. http://dx.doi.org/10.1016/0039-6028(92)90979-g.

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44

Alisi, Ikechukwu Ogadimma, Adamu Uzairu, and Stephen Eyije Abechi. "Free radical scavenging mechanism of 1,3,4-oxadiazole derivatives: thermodynamics of O–H and N–H bond cleavage." Heliyon 6, no. 3 (March 2020): e03683. http://dx.doi.org/10.1016/j.heliyon.2020.e03683.

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45

Jana, Anukul, Ina Objartel, Herbert W. Roesky, and Dietmar Stalke. "Cleavage of a N−H Bond of Ammonia at Room Temperature by a Germylene." Inorganic Chemistry 48, no. 3 (February 2, 2009): 798–800. http://dx.doi.org/10.1021/ic801964u.

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46

Xu, Wentao, Gaobo Hu, Pengxiang Xu, Yuxing Gao, Yingwu Yin, and Yufen Zhao. "Palladium-Catalyzed CP Cross-Coupling of Arylhydrazines with H-PhosphonatesviaCN Bond Cleavage." Advanced Synthesis & Catalysis 356, no. 14-15 (August 1, 2014): 2948–54. http://dx.doi.org/10.1002/adsc.201400155.

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47

Hakanoglu, Can, Feng Zhang, Abbin Antony, Aravind Asthagiri, and Jason F. Weaver. "Selectivity in the initial C–H bond cleavage of n-butane on PdO(101)." Physical Chemistry Chemical Physics 15, no. 29 (2013): 12075. http://dx.doi.org/10.1039/c3cp50659b.

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48

Tnay, Ya Lin, Gim Yean Ang, and Shunsuke Chiba. "ChemInform Abstract: Copper-Catalyzed Aerobic Radical C-C Bond Cleavage of N-H Ketimines." ChemInform 47, no. 4 (January 2016): no. http://dx.doi.org/10.1002/chin.201604043.

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49

Deng, Danfeng, Bowen Hu, Min Yang, and Dafa Chen. "Unusual C–O bond cleavage of aromatic ethers in ruthenium complexes bearing a 2-alkoxypyridyl fragment." Dalton Transactions 48, no. 36 (2019): 13614–21. http://dx.doi.org/10.1039/c9dt03020d.

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50

Zhou, Yao, Ya Wang, Zhiyi Song, Tamaki Nakano, and Qiuling Song. "Cu-catalyzed C–N bond cleavage of 3-aminoindazoles for the C–H arylation of enamines." Organic Chemistry Frontiers 7, no. 1 (2020): 25–29. http://dx.doi.org/10.1039/c9qo01177c.

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