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Journal articles on the topic 'Metalation'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 June 2025

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1

Balkenhohl, Moritz, and Paul Knochel. "Regioselective C–H Activation of Substituted Pyridines and other Azines using Mg- and Zn-TMP-Bases." SynOpen 02, no. 01 (2018): 0078–95. http://dx.doi.org/10.1055/s-0036-1591966.

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The metalation of substituted pyridines, diazines and related N-heterocycles using TMPMgCl·LiCl, TMP2Mg·2LiCl, TMPZnCl·LiCl or TMP2Zn·2LiCl2·2MgCl2 (TMP = 2,2,6,6-tetramethylpiperidyl) in the presence or absence of a Lewis acid is reviewed. Contents 1 Introduction2 Magnesiation of Pyridines and Related Azines2.1 Magnesiations using TMPMgCl·LiCl2.2 Magnesiations using TMP2Mg·2LiCl and Related Bases2.3 BF3·OEt2 Promoted Metalations of Pyridines3 Zincation of Pyridines and Related Azines using TMPZnCl·LiCl and TMP2Zn·2LiCl·2MgCl2 4 Metalation of Pyridines using other TMP-Bases5 Magnesiation and Zincation of Diazines6 Conclusion

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2

Quéguiner, Guy, Corinne Fruit, Alain Turck, and Nelly Plé. "Metalation of Pyrazinethiocarboxamides. Metalation of Diazines XXVI." HETEROCYCLES 51, no. 10 (1999): 2349. http://dx.doi.org/10.3987/com-99-8625.

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3

Grazia Cabiddu, Maria, Salvatore Cabiddu, Enzo Cadoni, Rita Cannas, Claudia Fattuoni, and Stefana Melis. "Metalation reactions. XXIV. Metalation of (vinylthio)benzene." Tetrahedron 54, no. 46 (1998): 14095–104. http://dx.doi.org/10.1016/s0040-4020(98)00869-2.

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4

Cabiddu, S., C. Floris, G. Gelli, and S. Melis. "Metalation reactions." Journal of Organometallic Chemistry 366, no. 1-2 (1989): 1–9. http://dx.doi.org/10.1016/0022-328x(89)87310-3.

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5

Cabiddu, S., C. Fattuoni, C. Floris, G. Gelli, and S. Melis. "Metalation reactions." Journal of Organometallic Chemistry 419, no. 1-2 (1991): 1–8. http://dx.doi.org/10.1016/0022-328x(91)86159-n.

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6

Plé, N., A. Turck, A. Heynderickx, and G. Quéguiner. "Synthesis and metalation of trifluoromethylpyrimidines. Metalation of diazines.XVI." Journal of Heterocyclic Chemistry 34, no. 2 (1997): 551–56. http://dx.doi.org/10.1002/jhet.5570340234.

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7

Ketels, Marthe, Dorothée Ziegler, and Paul Knochel. "Selective Zincation of 1,2-Dicyanobenzene and Related Benzonitriles in Continuous Flow Using In Situ Trapping Metalations." Synlett 28, no. 20 (2017): 2817–22. http://dx.doi.org/10.1055/s-0036-1588837.

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A mild and general metalation procedure for the functionalization of 1,2-dicyanobenzene and related polyfunctionalized benzonitriles using a commercially available continuous flow setup is reported. The addition of TMPLi (TMP = 2,2,6,6-tetramethylpiperidyl) to a mixture of an aromatic substrate with a metallic salt such as ZnCl2 under appropriate conditions (0 °C, 20 s) leads to fast in situ lithiation of the arene followed by transmetalation with ZnCl2 to afford the corresponding functionalized arylzinc compound that were trapped with various electrophiles in high yields. The reaction scope of these in situ trapping metalations in flow is broader and needs less equivalents of the base and the metal salt than the corresponding batch procedure.

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8

Blangetti, Marco, Patricia Fleming, and Donal F. O'Shea. "Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes." Beilstein Journal of Organic Chemistry 7 (September 9, 2011): 1249–54. http://dx.doi.org/10.3762/bjoc.7.145.

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A new two-step general approach to [2.2]metacyclophane synthesis from substituted m-xylenes is described. The strategy employs a selective benzylic metalation and oxidative C–C bond formation for both synthetic operations. Regioselective benzylic metalation is achieved using the BuLi, KOt-Bu, TMP(H) (2,2,6,6-tetramethylpiperidine) combination (LiNK metalation conditions) and oxidative coupling with 1,2-dibromoethane. The synthetic ease of this approach compares favourably with previously reported methods and allows for ready access to potentially useful planar chiral derivatives.

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9

Turck, A., N. Plé, D. Trohay, B. Ndzi, and G. Quéguiner. "Metalation of diazines.VI. Metalation of pivaloylaminopyrazine andN-t-butylpyrazinamide. Unusual regioselectivity in the metalation reaction." Journal of Heterocyclic Chemistry 29, no. 4 (1992): 699–702. http://dx.doi.org/10.1002/jhet.5570290404.

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10

Fu, J. m., B. p. Zhao, M. J. Sharp, and V. Snieckus. "ortho and remote metalation – cross coupling strategies. Total synthesis of the naturally occurring fluorenone dengibsinin and the azafluoranthene alkaloid imeluteine." Canadian Journal of Chemistry 72, no. 1 (1994): 227–36. http://dx.doi.org/10.1139/v94-035.

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The total synthesis of the naturally occurring fluorenone, dengibsinin (7a), and the azafluoranthene alkaloid, imeluteine (30e), is described. Using combined ortho metalation – cross coupling sequences that terminate in Friedel–Crafts (18b → 6d) and remote metalation (21a,b → 6c,d) reactions, the synthesis of fluorenone dimethyl ethers 6c and 6d is reported. 6c and 6d were shown not to be identical to dengibsinin dimethyl ether and dengibsin dimethyl ether, respectively, derived from the natural products. This work, together with synthetic and structural evidence from Sargent and Talapatra, led to the reassignment of structures for dengibsinin (7a) and dengibsin (7b). Using the metalation – cross coupling approach, the synthesis of the reassigned dengibsinin (7a) is presented. Two alternate unsuccessful approaches to imeluteine are briefly described (31 + 32 and 33 + 34). The successful approach incorporates the remote metalation – double cyclization, 43 → 44, as the key step.

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11

Wong, Daisy L., Amelia T. Yuan, Natalie C. Korkola, and Martin J. Stillman. "Interplay between Carbonic Anhydrases and Metallothioneins: Structural Control of Metalation." International Journal of Molecular Sciences 21, no. 16 (2020): 5697. http://dx.doi.org/10.3390/ijms21165697.

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Carbonic anhydrases (CAs) and metallothioneins (MTs) are both families of zinc metalloproteins central to life, however, they coordinate and interact with their Zn2+ ion cofactors in completely different ways. CAs and MTs are highly sensitive to the cellular environment and play key roles in maintaining cellular homeostasis. In addition, CAs and MTs have multiple isoforms with differentiated regulation. This review discusses current literature regarding these two families of metalloproteins in carcinogenesis, with a dialogue on the association of these two ubiquitous proteins in vitro in the context of metalation. Metalation of CA by Zn-MT and Cd-MT is described. Evidence for protein–protein interactions is introduced from changes in metalation profiles of MT from electrospray ionization mass spectrometry and the metalation rate from stopped-flow kinetics. The implications on cellular control of pH and metal donation is also discussed in the context of diseased states.

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12

Slocum, D. W., Seth Dumbris, Scott Brown, et al. "Metalation in hydrocarbon solvents: the mechanistic aspects of substrate-promoted ortho-metalations." Tetrahedron 59, no. 41 (2003): 8275–84. http://dx.doi.org/10.1016/j.tet.2003.07.010.

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13

Mulvey, Robert E. "Avant-Garde Metalating Agents: Structural Basis of Alkali-Metal-Mediated Metalation." Accounts of Chemical Research 42, no. 6 (2009): 743–55. http://dx.doi.org/10.1021/ar800254y.

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14

Quéguiner, Guy, Alain Turck, and Nelly Plé. "Metalation of Diazines." HETEROCYCLES 37, no. 3 (1994): 2149. http://dx.doi.org/10.3987/rev-93-sr20.

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15

Ito, Yoshihiko, and Masahiro Murakami. "Metalation of Isocyanides." Synlett 1990, no. 05 (1990): 245–50. http://dx.doi.org/10.1055/s-1990-21050.

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16

Turck, A., D. Trohay, L. Mojovic, N. Plé, and G. Quéguiner. "Metalation of diazines." Journal of Organometallic Chemistry 412, no. 3 (1991): 301–10. http://dx.doi.org/10.1016/0022-328x(91)86074-z.

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17

Ngu, Thanh T., and Martin J. Stillman. "Metalation of metallothioneins." IUBMB Life 61, no. 4 (2009): 438–46. http://dx.doi.org/10.1002/iub.182.

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18

Ngu, Thanh T., and Martin J. Stillman. "Metalation of metallothioneins." IUBMB Life 61, no. 4 (2009): spcone. http://dx.doi.org/10.1002/iub.202.

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19

CABIDDU, M. G., S. CABIDDU, E. CADONI, R. CANNAS, C. FATTUONI, and S. MELIS. "ChemInform Abstract: Metalation Reactions. Part 24. Metalation of (Vinylthio)benzene." ChemInform 30, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.199910098.

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20

Fruit, Corinne, Alain Turck, Nelly Ple, and Guy Queguiner. "ChemInform Abstract: Metalation of Diazines. Part 26. Metalation of Pyrazinethiocarboxamides." ChemInform 31, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.200005169.

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21

Fu, Jian-min, and Victor Snieckus. "The directed ortho metalation - palladium catalyzed cross coupling connection. A general regiospecific route to 9-phenanthrols and phenanthrenes. Exploratory further metalation." Canadian Journal of Chemistry 78, no. 6 (2000): 905–19. http://dx.doi.org/10.1139/v00-055.

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A new general and regiospecific synthesis of 9-phenanthrols (1 +2 [Formula: see text] 3 [Formula: see text] 4, Scheme 1, Table 1) proceeding by a Directed ortho Metalation (DoM), Suzuki-Miyaura cross coupling, and a new LDA-mediated Directed remote Metalation sequence is described. The facile Pd-catalyzed hydrogenolysis of the phenanthrols 4 into the corresponding phenanthrenes 5 via their triflates 18 translates the original DoM regioselectivity also into a general synthesis of phenanthrenes (Table 2). Further DoM (19 [Formula: see text]20, 21; 24 [Formula: see text]25), cross coupling (20c [Formula: see text]23), as well as oxidation - ring contraction (4b, 4f [Formula: see text]28a, 28b) chemistry of phenanthrene derivatives is reported.Key words: 9-phenanthrols, directed ortho metalation, Suzuki cross coupling, synthesis.

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22

Cai, Xiongwei, Stephen Brown, Peter Hodson, and Victor Snieckus. "Regiospecific synthesis of alkylphenanthrenes using a combined directed ortho and remote metalation SuzukiMiyaura cross coupling strategy." Canadian Journal of Chemistry 82, no. 2 (2004): 195–205. http://dx.doi.org/10.1139/v03-179.

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Using a combined directed ortho metalation (DoM) SuzukiMiyaura cross coupling directed remote metalation (DreM) approach, the alkylphenanthrenes (APs) 1-methyl- (5a), 1,7-dimethyl- (5b), 2,7-dimethyl- (5c), 7-ethyl-1-methyl- (15), and 7-tert-butyl-1-methylphenanthrenes (27) have been synthesized in four to seven steps and 21%36% overall yields. In contrast to classical protocols, this method, which may be scaled to gram quantities, provides single isomers of APs in high purity of value as analytical standards for environmental studies. Aminocarbonylation of triflates to N,N-diethylbenzamides (9 [Formula: see text] 10) and anionic Fries rearrangement (23 [Formula: see text] 24) provide other potential links to DoM chemistry.Key words: phenanthrene, directed ortho metalation, SuzukiMiyaura cross coupling, synthesis, polycyclic aromatic hydrocarbon, carbonylation.

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23

Mojovic, Ljubica, Alain Turck, Nelly Plé, Muriel Dorsy, Bruno Ndzi, and Guy Quéguiner. "Metalation of diazines XVII Very hindered bases as new metalating agents, Improvement of regioselectivity for the metalation of 3-chloro-6-methoxypyridazine." Tetrahedron 52, no. 31 (1996): 10417–26. http://dx.doi.org/10.1016/0040-4020(96)00568-6.

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24

CABIDDU, S., C. FATTUONI, C. FLORIS, G. GELLI, and S. MELIS. "ChemInform Abstract: Metalation Reactions. Part 15. Regioselective Metalation of (Alkylthio) fluorobenzenes." ChemInform 23, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199206153.

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25

Foster, Andrew W., Tessa R. Young, Peter T. Chivers, and Nigel J. Robinson. "Protein metalation in biology." Current Opinion in Chemical Biology 66 (February 2022): 102095. http://dx.doi.org/10.1016/j.cbpa.2021.102095.

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26

Luliński, Sergiusz, and Janusz Serwatowski. "Regiospecific Metalation of Oligobromobenzenes." Journal of Organic Chemistry 68, no. 13 (2003): 5384–87. http://dx.doi.org/10.1021/jo0340511.

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27

Lash, Timothy D. "Metalation of Carbaporphyrinoid Systems." Macroheterocycles 1, no. 1 (2008): 9–20. http://dx.doi.org/10.6060/mhc2008.1.9.

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28

Plé, N., A. Turck, K. Couture, and G. Queguiner. "Metalation of diazines X." Tetrahedron 50, no. 34 (1994): 10299–308. http://dx.doi.org/10.1016/s0040-4020(01)81762-2.

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29

PLE, N., A. TURCK, A. HEYNDERICKX, and G. QUEGUINER. "ChemInform Abstract: Metalation of Diazines. Part 16. Synthesis and Metalation of Trifluoromethylpyrimidines." ChemInform 28, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199738199.

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30

TURCK, A., N. PLE, D. TROHAY, B. NDZI, and G. QUEGUINER. "ChemInform Abstract: Metalation of Diazines. Part 6. Metalation of Pivaloylaminopyrazine and N-tert-Butylpyrazinamide. Unusual Regioselectivity in the Metalation Reaction." ChemInform 23, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199248210.

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31

Talko, Alicja, Damian Antoniak, and Michał Barbasiewicz. "Directed ortho-Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates." Synthesis 51, no. 11 (2019): 2278–86. http://dx.doi.org/10.1055/s-0037-1610877.

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Studies on directed ortho-metalation (DoM) of arenesulfonyl fluorides (ArSO2F) with in situ electrophile trapping are presented. Under optimized conditions (LDA, THF, –78 °C), a series of model substrates was mono- and difunctionalized with trimethylsilyl chloride in good yields. The synthetic results reveal powerful directing character of the SO2F group, being ahead of bromine and methoxy substituents. Under the same metalation conditions, aryl fluorosulfates (ArOSO2F) display fragmentation to arynes and migration of the SO2F group to the ortho position (anionic thia-Fries rearrangement).

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32

Scheller, Judith S., Gordon W. Irvine, and Martin J. Stillman. "Unravelling the mechanistic details of metal binding to mammalian metallothioneins from stoichiometric, kinetic, and binding affinity data." Dalton Transactions 47, no. 11 (2018): 3613–37. http://dx.doi.org/10.1039/c7dt03319b.

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33

Snieckus, Victor, and Claude Quesnelle. "The Directed ortho Metalation (DoM)–Cross-Coupling Connection: Synthesis of Polyfunctional Biaryls." Synthesis 50, no. 22 (2018): 4413–28. http://dx.doi.org/10.1055/s-0037-1610273.

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A comparative evaluation of the combined directed ortho metalation (DoM)–Suzuki–Miyaura and DoM–Negishi cross-coupling reactions with aryl triflates for the synthesis of substituted biaryls is described. Both ortho-zinc and ortho-boron aryl directed metalation group (DMG = CON(i-Pr)2, OCONEt2, OMOM, NHBoc) substrates were evaluated. The superiority of the DoM–Negishi over the DoM–Suzuki–Miyaura reaction in operational convenience and mild reaction conditions is noted. Orthogonal Negishi and Suzuki–Miyaura with Corriu–Kumada reactions for the synthesis of a teraryl derivative is also reported.

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34

Ple, Nelly, Alain Turck, Karine Couture, and Guy Queguiner. "Diazines 13: Metalation without Ortho-Directing Group - Functionalization of Diazines via Direct Metalation." Journal of Organic Chemistry 60, no. 12 (1995): 3781–86. http://dx.doi.org/10.1021/jo00117a033.

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35

CABIDDU, S., C. FATTUONI, C. FLORIS, G. GELLI, and S. MELIS. "ChemInform Abstract: Metalation Reactions. Part 18. Regioselective Metalation of (Alkylthio) benzenes by Superbases." ChemInform 24, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199312130.

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36

Evans, Jack D., Christopher J. Sumby, and Christian J. Doonan. "Post-synthetic metalation of metal–organic frameworks." Chem. Soc. Rev. 43, no. 16 (2014): 5933–51. http://dx.doi.org/10.1039/c4cs00076e.

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37

Jin, Jiarui. "Porphyrin-based metal–organic framework catalysts for photoreduction of CO2: understanding the effect of node connectivity and linker metalation on activity." New Journal of Chemistry 44, no. 36 (2020): 15362–68. http://dx.doi.org/10.1039/d0nj03507f.

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38

Llopart, Carme Cantos, Conchita Ferrer, and John A. Joule. "Lithiation of 1-arylimidazol-2(1H)-ones and 1-aryl-4,5-dihydroimidazol-2(1H)-ones." Canadian Journal of Chemistry 82, no. 11 (2004): 1649–61. http://dx.doi.org/10.1139/v04-137.

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1-Arylimidazol-2(1H)-ones are shown to be readily lithiated, using 2 mol equiv. of n-butyllithium, on the benzene ring, ortho to the heterocycle. 1-Aryl-4,5-dihydroimidazol-2(1H)-ones also undergo metalation on the aromatic substitutuent ortho to the heterocycle, but less efficiently. 1-Aryl-3-methylimidazol-2(1H)-ones are lithiated on the heterocyclic ring and then on the benzene ring ortho to the heterocycle. No ortho-directing effect was found for 1-aryl-4,5-dihydro-3-methylimidazol-2(1H)-ones.Key words: ortho-lithation, ureas for directed ortho metalation, 1-arylimidazol-2-ones, 1-arylimidazolidin-2-ones.

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39

TURCK, A., N. PLE, V. TALLON, and G. QUEGUINER. "ChemInform Abstract: Metalation of Diazines. Part 14. First o-Directed Metalation of Cinnolines. Metalation of 3-, 4-Chloro, and 3-, 4-Methoxycinnolines." ChemInform 27, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199611193.

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40

Sullivan, Matthew P., Michael Groessl, Samuel M. Meier, Richard L. Kingston, David C. Goldstone, and Christian G. Hartinger. "The metalation of hen egg white lysozyme impacts protein stability as shown by ion mobility mass spectrometry, differential scanning calorimetry, and X-ray crystallography." Chemical Communications 53, no. 30 (2017): 4246–49. http://dx.doi.org/10.1039/c6cc10150j.

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41

Fan, Zhoulong, Heng Lu, Zhen Cheng, and Ao Zhang. "Ligand-promoted ruthenium-catalyzed meta C–H chlorination of arenes using N-chloro-2,10-camphorsultam." Chemical Communications 54, no. 47 (2018): 6008–11. http://dx.doi.org/10.1039/c8cc03195a.

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42

Nebe, Marco M., Sina Zinn, and Till Opatz. "A short and modular approach towards 3,5-disubstituted indolizidine alkaloids." Organic & Biomolecular Chemistry 14, no. 29 (2016): 7084–91. http://dx.doi.org/10.1039/c6ob01308b.

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43

Melzer, Benedikt C., and Franz Bracher. "A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines." Beilstein Journal of Organic Chemistry 13 (August 8, 2017): 1564–71. http://dx.doi.org/10.3762/bjoc.13.156.

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Oxoisoaporphine alkaloids are conveniently prepared via direct ring metalation of alkoxy-substituted isoquinolines at C-1, followed by reaction with iodine. Subsequent Suzuki cross-coupling of the resulting 1-iodoisoquinolines to methyl 2-(isoquinolin-1-yl)benzoates and intramolecular acylation of the corresponding carboxylic acids with Eaton’s reagent afforded five alkaloids of the oxoisoaporphine type. The yield of the cyclization step strongly depends on the electrophilic properties of ring B. An alternative cyclization protocol via directed remote metalation of ester and amide intermediates was investigated thoroughly, but found to be not feasible. Two of the alkaloids showed strong cytotoxicity against the HL-60 tumor cell line.

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44

Laufer, Radoslaw, Ulrich Veith, Nicholas J. Taylor, and Victor Snieckus. "(–)-Sparteine-mediated stereoselective directed ortho metalation of ferrocene diamides." Canadian Journal of Chemistry 84, no. 2 (2006): 356–69. http://dx.doi.org/10.1139/v06-008.

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The utility of (–)-sparteine-mediated directed ortho metalation (DoM) has been investigated in stereoselective preparation of planar chiral ferrocenes derived from 1,1′-N,N,N′,N′-tetraisopropylferrocenedicarboxamide (5). In the synthesis of C2-symmetric analogs of 5, the protocol (base, solvent, and two-step DoM) was found to be crucial for obtaining high enantio- and diastereo-selectivities of the products. A variety of highly enantioenriched mono and doubly functionalized derivatives of 5 have been synthesized. The synthetic applications of these compounds as chiral ligands in asymmetric alkylation of aldehydes and asymmetric palladium-catalyzed allylic substitutions have been demonstrated.Key words: directed ortho metalation, stereoselective deprotonation, ferrocene ligands, asymmetric catalysis.

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45

Dupas, Georges, Cyril Papamicaël, Guy Quéguiner, and Jean Bourguignon. "Regioselective Metalation of g-Carbolines." HETEROCYCLES 49, no. 1 (1998): 361. http://dx.doi.org/10.3987/com-98-s45.

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46

Jeans, Rebekah J., Antony P. Y. Chan, Ashton H. Murrell, Heather A. Chouman, Georgina M. Rosair, and Alan J. Welch. "Metalation of Bis(meta-carborane)." Journal of Organometallic Chemistry 950 (October 2021): 121980. http://dx.doi.org/10.1016/j.jorganchem.2021.121980.

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47

Kießling, Tilmann, and Karlheinz Sünkel. "Metalation Studies on Titanocene Dithiolates." Inorganics 6, no. 3 (2018): 85. http://dx.doi.org/10.3390/inorganics6030085.

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Titanocene bis-arylthiolates [(C5H4X)(C5H4Y)Ti(SC6H4R)2] (X,Y = H, Cl; R = H, Me) can be prepared from the corresponding titanocene dichlorides by reacting with the thiols in the presence of DABCO as a base. They react with n-butyl lithium to give unstable Ti(III) radical anions. While the unsubstituted thiolates (X = Y = R = H) react with lithium Di-isopropylamide by decomposing to dimeric fulvalene-bridged and thiolate-bridged Ti(III) compounds, the ring-chlorinated compounds can be deprotonated with LDA and give appropriate electrophiles di-substituted and tri-substituted titanocene dithiolates.

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48

Poindexter, Graham S., Michael A. Foley, and Joseph F. Licause. "Metalation of 1,4-dihydropyridine esters." Tetrahedron Letters 30, no. 26 (1989): 3393–96. http://dx.doi.org/10.1016/s0040-4039(00)99253-0.

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49

Azzena, Ugo, Luciano Pilo, and Alessandra Sechi. "Metalation of arylmethyl alkyl ethers." Tetrahedron 54, no. 40 (1998): 12389–98. http://dx.doi.org/10.1016/s0040-4020(98)00758-3.

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50

Harmata, Michael, and Nathan Calkins. "Further Studies of Benzothiazine Metalation." Synthesis 45, no. 13 (2013): 1785–90. http://dx.doi.org/10.1055/s-0033-1338444.

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