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Journal articles on the topic 'Chemoselectivity'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Wang, Juping, Kangcheng Zheng, Ting Li, and Xiaojing Zhan. "Mechanism and Chemoselectivity of Mn-Catalyzed Intramolecular Nitrene Transfer Reaction: C–H Amination vs. C=C Aziridination." Catalysts 10, no. 3 (March 4, 2020): 292. http://dx.doi.org/10.3390/catal10030292.

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The reactivity, mechanism and chemoselectivity of the Mn-catalyzed intramolecular C–H amination versus C=C aziridination of allylic substrate cis-4-hexenylsulfamate are investigated by BP86 density functional theory computations. Emphasis is placed on the origins of high reactivity and high chemoselectivity of Mn catalysis. The N p orbital character of frontier orbitals, a strong electron-withdrawing porphyrazine ligand and a poor π backbonding of high-valent MnIII metal to N atom lead to high electrophilic reactivity of Mn-nitrene. The calculated energy barrier of C–H amination is 9.9 kcal/mol lower than that of C=C aziridination, which indicates that Mn-based catalysis has an excellent level of chemoselectivity towards C–H amination, well consistent with the experimental the product ratio of amintion-to-aziridination I:A (i.e., (Insertion):(Aziridination)) >20:1. This extraordinary chemoselectivity towards C–H amination originates from the structural features of porphyrazine: a rigid ligand with the big π-conjugated bond. Electron-donating substituents can further increase Mn-catalyzed C–H amination reactivity. The controlling factors found in this work may be considered as design elements for an economical and environmentally friendly C–H amination system with high reactivity and high chemoselectivity.

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2

Ho, Tse-Lok. "Chemoselectivity of organometallic reactions." Tetrahedron 41, no. 1 (January 1985): 3–86. http://dx.doi.org/10.1016/s0040-4020(01)83470-0.

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3

Marigo, Mauro, and Paolo Melchiorre. "Chemoselectivity in Asymmetric Aminocatalysis." ChemCatChem 2, no. 6 (June 7, 2010): 621–23. http://dx.doi.org/10.1002/cctc.201000110.

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4

Zhang, Sai, Zhaoming Xia, Ting Ni, Huan Zhang, Chao Wu, and Yongquan Qu. "Tuning chemical compositions of bimetallic AuPd catalysts for selective catalytic hydrogenation of halogenated quinolines." Journal of Materials Chemistry A 5, no. 7 (2017): 3260–66. http://dx.doi.org/10.1039/c6ta09916e.

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Au_1−xPd_x bimetallic catalysts with low Pd entities on CeO₂ nanorods delivered high activity and chemoselectivity for hydrogenation of halogenated quinolines. Improved chemoselectivity could be attributed to the selective adsorption configurations of halogenated quinolines on Au via tilted orientation rather than on Pd via flat orientation.

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5

Nahmany, Moshe, and Artem Melman. "Chemoselectivity in reactions of esterification." Organic & Biomolecular Chemistry 2, no. 11 (2004): 1563. http://dx.doi.org/10.1039/b403161j.

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6

Sinha, S. C., E. Keinan, and J. L. Reymond. "Antibody-catalyzed reversal of chemoselectivity." Proceedings of the National Academy of Sciences 90, no. 24 (December 15, 1993): 11910–13. http://dx.doi.org/10.1073/pnas.90.24.11910.

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7

Thygesen, Mikkel B., and Knud J. Jensen. "ChemInform Abstract: Chemoselectivity and Glyconanoparticles." ChemInform 44, no. 11 (March 8, 2013): no. http://dx.doi.org/10.1002/chin.201311226.

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8

Barak-Kulbak, Einav, Kerem Goren, and Moshe Portnoy. "Advantages of polymer-supported multivalent organocatalysts for the Baylis-Hillman reaction over their soluble analogues." Pure and Applied Chemistry 86, no. 11 (November 1, 2014): 1805–18. http://dx.doi.org/10.1515/pac-2014-0721.

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Abstract Immobilization of well-defined catalytic units onto insoluble support promises significant benefits, but frequently results in a reduced activity and selectivity of the heterogenized catalysts. Recently, we showed that introduction of a dendritic spacer between the support and the units could remedy the compromised activity and/or selectivity of heterogenized catalysts and, in particular, of the systems based on N-alkylated imidazoles. These catalysts exhibit an outstanding multivalency effect on the activity in the Baylis-Hillman reaction, while preserving very high chemoselectivity. In order to better understand this remarkable effect, we decided to synthesize and examine soluble analogues of the supported systems. These soluble catalysts display poor chemoselectivity, although it improves with the increase of the dendritic generation. Though the consumption of the limiting aldehyde reactant (conversion) displays the opposite trend, experiments demonstrated that the chemoselectivity is generation-dependent rather than conversion-dependent. A hydrophobic “pocket” effect was implicated as responsible for the differences between the polystyrene-bound and the soluble catalysts. An MS analysis of the crude reaction mixture revealed that the formation of multiple adducts, which incorporate several enone and several nitrobenzaldehyde fragments into a single molecular structure (as opposed to one-to-one stoichiometry of the Baylis-Hillman reaction), is responsible for the decline in the chemoselectivity.

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9

Ghinato, Simone, Giuseppe Dilauro, Filippo Maria Perna, Vito Capriati, Marco Blangetti, and Cristina Prandi. "Directed ortho-metalation–nucleophilic acyl substitution strategies in deep eutectic solvents: the organolithium base dictates the chemoselectivity." Chemical Communications 55, no. 54 (2019): 7741–44. http://dx.doi.org/10.1039/c9cc03927a.

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10

Yu, Haifeng, Dewen Dong, Yan Ouyang, and Qun Liu. "Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid as a 1,3-propanedithiol equivalent." Canadian Journal of Chemistry 83, no. 10 (October 1, 2005): 1741–45. http://dx.doi.org/10.1139/v05-184.

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Odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid (1c) was prepared and investigated in the thioacetalization of carbonyl compounds as a 1,3-propanedithiol equivalent. The results showed that the thioacetalization of various carbonyl compounds 2 with 1c proceeded smoothly and afforded the corresponding dithioacetals 3 in high yields (up to 99%) in the presence of acetyl chloride at room or reflux temperatures. Moreover, the thioacetalization exhibited high chemoselectivity between aldehydes and ketones. Key words: chemoselectivity, 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid, α-oxo ketene dithioacetal, 1,3-propanedithiol equivalent, thioacetalization.

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11

Rudolph, Matthias, Melissa Q. McCreery, Wolfgang Frey, and A. Stephen K. Hashmi. "High chemoselectivity in the phenol synthesis." Beilstein Journal of Organic Chemistry 7 (June 10, 2011): 794–801. http://dx.doi.org/10.3762/bjoc.7.90.

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Efforts to trap early intermediates of the gold-catalyzed phenol synthesis failed. Neither inter- nor intramolecularly offered vinyl groups, ketones or alcohols were able to intercept the gold carbenoid species. This indicates that the competing steps of the gold-catalyzed phenol synthesis are much faster than the steps of the interception reaction. In the latter the barrier of activation is higher. At the same time this explains the high tolerance of this very efficient and general reaction towards functional groups.

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12

Marigo, Mauro, and Paolo Melchiorre. "ChemInform Abstract: Chemoselectivity in Asymmetric Aminocatalysis." ChemInform 41, no. 36 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.201036248.

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13

Klimochkin, Yu N., M. V. Leonova, and E. A. Ivleva. "Chemoselectivity of Nitroxylation of Cage Hydrocarbons." Russian Journal of Organic Chemistry 56, no. 10 (October 2020): 1702–10. http://dx.doi.org/10.1134/s107042802010005x.

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14

Dominguez, A., N. Cabezas, J. M. Sánchez - Montero, and J. V. Sinisterra. "Chemoselectivity of chemically modified α-chymotrypsin." Tetrahedron 51, no. 6 (February 1995): 1827–44. http://dx.doi.org/10.1016/0040-4020(94)01060-d.

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15

Shu, Siwei, Meijie Huang, Jingxing Jiang, Ling-Bo Qu, Yan Liu, and Zhuofeng Ke. "Catalyzed or non-catalyzed: chemoselectivity of Ru-catalyzed acceptorless dehydrogenative coupling of alcohols and amines via metal–ligand bond cooperation and (de)aromatization." Catalysis Science & Technology 9, no. 9 (2019): 2305–14. http://dx.doi.org/10.1039/c9cy00243j.

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16

Li, Yunyi, Zhengxing Wu, Zheng Ling, Hongjin Chen, and Wanbin Zhang. "Mechanistic study of the solvent-controlled Pd(ii)-catalyzed chemoselective intermolecular 1,2-aminooxygenation and 1,2-oxyamination of conjugated dienes." Organic Chemistry Frontiers 6, no. 4 (2019): 486–92. http://dx.doi.org/10.1039/c8qo01288a.

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17

Liu, Jian-Biao, Xin Zhang, Ying-Ying Tian, Xin Wang, Xun-Kun Zhu, and De-Zhan Chen. "Mechanism and origins of ligand-controlled Pd(ii)-catalyzed regiodivergent carbonylation of alkynes." Dalton Transactions 48, no. 40 (2019): 15059–67. http://dx.doi.org/10.1039/c9dt03294k.

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18

Yoshida, Ryota, Katsuhiro Isozaki, Tomoya Yokoi, Nobuhiro Yasuda, Koichiro Sadakane, Takahiro Iwamoto, Hikaru Takaya, and Masaharu Nakamura. "ONO-pincer ruthenium complex-bound norvaline for efficient catalytic oxidation of methoxybenzenes with hydrogen peroxide." Organic & Biomolecular Chemistry 14, no. 31 (2016): 7468–79. http://dx.doi.org/10.1039/c6ob00969g.

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19

More, Kunal N., Tae-Hwan Lim, Julie Kang, and Dong-Jo Chang. "A Fluorogenic Assay: Analysis of Chemical Modification of Lysine and Arginine to Control Proteolytic Activity of Trypsin." Molecules 26, no. 7 (March 31, 2021): 1975. http://dx.doi.org/10.3390/molecules26071975.

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The chemical modification of amino acids plays an important role in the modulation of proteins or peptides and has useful applications in the activation and stabilization of enzymes, chemical biology, shotgun proteomics, and the production of peptide-based drugs. Although chemoselective modification of amino acids such as lysine and arginine via the insertion of respective chemical moieties as citraconic anhydride and phenyl glyoxal is important for achieving desired application objectives and has been extensively reported, the extent and chemoselectivity of the chemical modification of specific amino acids using specific chemical agents (blocking or modifying agents) has yet to be sufficiently clarified owing to a lack of suitable assay methodologies. In this study, we examined the utility of a fluorogenic assay method, based on a fluorogenic tripeptide substrate (FP-AA1-AA2-AA3) and the proteolytic enzyme trypsin, in determinations of the extent and chemoselectivity of the chemical modification of lysine or arginine. As substrates, we used two fluorogenic tripeptide probes, MeRho-Lys-Gly-Leu(Ac) (lysine-specific substrate) and MeRho-Arg-Gly-Leu(Ac) (arginine-specific substrate), which were designed, synthesized, and evaluated for chemoselective modification of specific amino acids (lysine and arginine) using the fluorogenic assay. The results are summarized in terms of half-maximal inhibitory concentrations (IC50) for the extent of modification and ratios of IC50 values (IC50arginine/IC50lysine and IC50lysine/IC50arginine) as a measure of the chemoselectivity of chemical modification for amino acids lysine and arginine. This novel fluorogenic assay was found to be rapid, precise, and reproducible for determinations of the extent and chemoselectivity of chemical modification.

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20

Ye, Zongren, Xiao Huang, Youxiang Shao, Jingxing Jiang, Ling-Bo Qu, Cunyuan Zhao, and Zhuofeng Ke. "One catalyst, multiple processes: ligand effects on chemoselective control in Ru-catalyzed anti-Markovnikov reductive hydration of terminal alkynes." Catalysis Science & Technology 9, no. 9 (2019): 2315–27. http://dx.doi.org/10.1039/c8cy02437e.

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21

Wang, Zichun, Kyung-Duk Kim, Cuifeng Zhou, Mengmeng Chen, Nobutaka Maeda, Zongwen Liu, Jeffrey Shi, Alfons Baiker, Michael Hunger, and Jun Huang. "Influence of support acidity on the performance of size-confined Pt nanoparticles in the chemoselective hydrogenation of acetophenone." Catalysis Science & Technology 5, no. 5 (2015): 2788–97. http://dx.doi.org/10.1039/c5cy00214a.

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22

Jin, Ming Yu, Sun Min Kim, Hui Mao, Do Hyun Ryu, Choong Eui Song, and Jung Woon Yang. "Chemoselective and repetitive intermolecular cross-acyloin condensation reactions between a variety of aromatic and aliphatic aldehydes using a robust N-heterocyclic carbene catalyst." Org. Biomol. Chem. 12, no. 10 (2014): 1547–50. http://dx.doi.org/10.1039/c3ob42486c.

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23

Liu, Ruzhang, Zhen Wei, Juan Wang, Yongmei Liu, and Huaiguo Xue. "Highly selective hydrosilylation of equilibrating allylic azides." Chemical Communications 56, no. 37 (2020): 5038–41. http://dx.doi.org/10.1039/d0cc01316a.

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24

Chen, Alexander N., and Sara E. Skrabalak. "Molecular-like selectivity emerges in nanocrystal chemistry." Dalton Transactions 49, no. 36 (2020): 12530–35. http://dx.doi.org/10.1039/d0dt01168a.

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25

Jiang, He-yan, and Xu-xu Zheng. "Tuning the chemoselective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines catalyzed by phosphine functionalized ionic liquid stabilized ruthenium nanoparticles." Catalysis Science & Technology 5, no. 7 (2015): 3728–34. http://dx.doi.org/10.1039/c5cy00293a.

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26

Li, Xue, Jun Xu, Shi-Jun Li, Ling-Bo Qu, Zhongjun Li, Yonggui Robin Chi, Donghui Wei, and Yu Lan. "Prediction of NHC-catalyzed chemoselective functionalizations of carbonyl compounds: a general mechanistic map." Chemical Science 11, no. 27 (2020): 7214–25. http://dx.doi.org/10.1039/d0sc01793k.

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27

Schammel, Marella H., Kayla R. Martin-Culet, Garrett A. Taggart, and John D. Sivey. "Structural effects on the bromination rate and selectivity of alkylbenzenes and alkoxybenzenes in aqueous solution." Physical Chemistry Chemical Physics 23, no. 31 (2021): 16594–610. http://dx.doi.org/10.1039/d1cp02422a.

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28

Traverssi, Miqueas G., Alicia B. Peñéñory, Oscar Varela, and Juan P. Colomer. "Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions." RSC Advances 11, no. 16 (2021): 9262–73. http://dx.doi.org/10.1039/d0ra09534f.

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29

Zuo, Youpeng, Xinwei He, Yi Ning, Lanlan Zhang, Yuhao Wu, and Yongjia Shang. "Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C–C or C–N bond cleavage." New Journal of Chemistry 42, no. 3 (2018): 1673–81. http://dx.doi.org/10.1039/c7nj03799f.

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30

Kawajiri, Takahiro, Reiya Ohta, Hiromichi Fujioka, Hironao Sajiki, and Yoshinari Sawama. "Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers." Chemical Communications 54, no. 4 (2018): 374–77. http://dx.doi.org/10.1039/c7cc08936h.

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31

Pei, Yuchen, Minda Chen, Xiaoliang Zhong, Tommy Yunpu Zhao, Maria-Jose Ferrer, Raghu V. Maligal-Ganesh, Tao Ma, et al. "Pairwise semi-hydrogenation of alkyne to cis-alkene on platinum-tin intermetallic compounds." Nanoscale 12, no. 15 (2020): 8519–24. http://dx.doi.org/10.1039/d0nr00920b.

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32

Zhou, Lin, Li Yang, Yanwen Zhang, Alexander M. Kirillov, Ran Fang, and Bing Han. "Theoretical study on the mechanism and chemoselectivity in gold(i)-catalyzed cycloisomerization of β,β-disubstituted ortho-(alkynyl)styrenes." Organic Chemistry Frontiers 6, no. 15 (2019): 2701–12. http://dx.doi.org/10.1039/c9qo00534j.

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33

Herraiz, Ana G., and Marcos G. Suero. "A transition-metal-free & diazo-free styrene cyclopropanation." Chemical Science 10, no. 40 (2019): 9374–79. http://dx.doi.org/10.1039/c9sc02749a.

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34

Paulisch, Tiffany O., Felix Strieth-Kalthoff, Christian Henkel, Lena Pitzer, Dirk M. Guldi, and Frank Glorius. "Chain propagation determines the chemo- and regioselectivity of alkyl radical additions to C–O vs. C–C double bonds." Chemical Science 11, no. 3 (2020): 731–36. http://dx.doi.org/10.1039/c9sc04846d.

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35

Sabet-Sarvestani, H., H. Eshghi, M. Bakavoli, M. Izadyar, and M. Rahimizadeh. "Theoretical investigation of the chemoselectivity and synchronously pyrazole ring formation mechanism from ethoxymethylenemalononitrile and hydrazine hydrate in the gas and solvent phases: DFT, meta-GGA studies and NBO analysis." RSC Adv. 4, no. 82 (2014): 43485–95. http://dx.doi.org/10.1039/c4ra06316c.

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36

Liu, Ruzhang, Yuanyuan Zhang, and Jun Xu. "Selective hydroboration of equilibrating allylic azides." Chemical Communications 57, no. 71 (2021): 8913–16. http://dx.doi.org/10.1039/d1cc02520a.

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37

Suárez-Castillo, Oscar R., Manuel García-Velgara, Martha S. Morales-Ríos, and Pedro Joseph-Nathan. "Chemoselective intramolecular annulation of 3-alkylindolines into dihydro or tetrahydrofuro[2,3-b]indoles." Canadian Journal of Chemistry 75, no. 7 (July 1, 1997): 959–64. http://dx.doi.org/10.1139/v97-115.

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3-Alkyl-2-hydroxyindolines, conveniently prepared from 2-hydroxyindolenines and a Grignard reagent, cyclize in the aprotic solvent tetrahydrofuran to afford tetrahydro-3-cyano-2-oxofuro[2,3-b]indoles, while in the protic solvent methanol the chemoselectivity changed to give dihydro-2-amino-3-carbomethoxyfuro[2,3-b]indoles. The steric effect of the alkyl group on the reactivity of 3-alkyl-2-hydroxyindolines is discussed for both processes. The ring transformation of tetrahydro-3-cyano-2-oxofuro[2,3-b]indoles into dihydro-2-amino-3-carbomethoxyfuro[2,3-b]indoles via γ-lactone imines is also discussed. Keywords: furo[2,3-b]indoles, α-cyano-γ-lactones, chemoselectivity, ring transformation, β-enamino esters.

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38

Ni, Ke, Ling-Guo Meng, Hongjie Ruan, and Lei Wang. "Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: synthesis of propargyl alcohols and α-ketoesters." Chemical Communications 55, no. 58 (2019): 8438–41. http://dx.doi.org/10.1039/c9cc04090k.

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39

Gao, Weiwei, Xueyan Zhang, Xingze Xie, and Shengtao Ding. "One simple Ir/hydrosilane catalytic system for chemoselective isomerization of 2-substituted allylic ethers." Chemical Communications 56, no. 13 (2020): 2012–15. http://dx.doi.org/10.1039/c9cc09055j.

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40

Dubey, Kshatresh Dutta, Binju Wang, Manu Vajpai, and Sason Shaik. "MD simulations and QM/MM calculations show that single-site mutations of cytochrome P450BM3 alter the active site’s complexity and the chemoselectivity of oxidation without changing the active species." Chemical Science 8, no. 8 (2017): 5335–44. http://dx.doi.org/10.1039/c7sc01932g.

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41

Yang, Yi-Meng, Zhi-Min Dang, and Hai-Zhu Yu. "Density functional theory investigation on Pd-catalyzed cross-coupling of azoles with aryl thioethers." Organic & Biomolecular Chemistry 14, no. 19 (2016): 4499–506. http://dx.doi.org/10.1039/c6ob00607h.

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42

Yang, Junfeng, Yixiao Shen, Yang Jie Lim, and Naohiko Yoshikai. "Divergent ring-opening coupling between cyclopropanols and alkynes under cobalt catalysis." Chemical Science 9, no. 34 (2018): 6928–34. http://dx.doi.org/10.1039/c8sc02074d.

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43

Luo, Kui, Ling Zhang, Huanfeng Jiang, Lianfen Chen, and Shifa Zhu. "Selectivity-switchable construction of benzo-fused polycyclic compounds through a gold-catalyzed reaction of enyne-lactone." Chemical Communications 54, no. 15 (2018): 1893–96. http://dx.doi.org/10.1039/c7cc09786g.

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44

Deng, Qianqian, Shi-Jun Li, Donghui Wei, and Yu Lan. "Insights into Lewis base-catalyzed chemoselective [3 + 2] and [3 + 4] annulation reactions of MBH carbonates." Organic Chemistry Frontiers 7, no. 14 (2020): 1828–36. http://dx.doi.org/10.1039/d0qo00457j.

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45

Wang, Congcong, Shi-Jun Li, Qiao-Chu Zhang, Donghui Wei, and Lina Ding. "Insights into isothiourea-catalyzed asymmetric [3 + 3] annulation of α,β-unsaturated aryl esters with 2-acylbenzazoles: mechanism, origin of stereoselectivity and switchable chemoselectivity." Catalysis Science & Technology 10, no. 11 (2020): 3664–69. http://dx.doi.org/10.1039/d0cy00295j.

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46

Yingcharoen, Prapussorn, Wuttichai Natongchai, Albert Poater, and Valerio D' Elia. "Intertwined chemistry of hydroxyl hydrogen-bond donors, epoxides and isocyanates in the organocatalytic synthesis of oxazolidinones versus isocyanurates: rational catalytic investigation and mechanistic understanding." Catalysis Science & Technology 10, no. 16 (2020): 5544–58. http://dx.doi.org/10.1039/d0cy00987c.

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47

Zhu, Li-Han, Hai-Yan Yuan, Wen-Liang Li, and Jing-Ping Zhang. "A computational mechanistic study of substrate-controlled competitive O–H and C–H insertion reactions catalyzed by dirhodium(ii) carbenoids: insight into the origin of chemoselectivity." Organic Chemistry Frontiers 5, no. 15 (2018): 2353–63. http://dx.doi.org/10.1039/c8qo00475g.

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48

Pei, Guojing, Yuxia Liu, Guang Chen, Xiangai Yuan, Yuan-Ye Jiang, and Siwei Bi. "Unveiling the mechanisms and secrets of chemoselectivities in Au(i)-catalyzed diazo-based couplings with aryl unsaturated aliphatic alcohols." Catalysis Science & Technology 8, no. 17 (2018): 4450–62. http://dx.doi.org/10.1039/c8cy01352g.

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49

Shi, Qianqian, Wei Wang, Yang Wang, Yu Lan, Changsheng Yao, and Donghui Wei. "Prediction on the origin of chemoselectivity in Lewis base-mediated competition cyclizations between allenoates and chalcones: a computational study." Organic Chemistry Frontiers 6, no. 15 (2019): 2692–700. http://dx.doi.org/10.1039/c9qo00606k.

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50

Gao, Feng, Byeong-Seon Kim, and Patrick J. Walsh. "Chemoselective palladium-catalyzed deprotonative arylation/[1,2]-Wittig rearrangement of pyridylmethyl ethers." Chemical Science 7, no. 2 (2016): 976–83. http://dx.doi.org/10.1039/c5sc02739j.

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