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Journal articles on the topic 'Ortho- metalation'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

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-arylimid

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2

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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3

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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4

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 [

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5

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-diethylbenzam

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6

Li, Gang, Xingxing Ma, Chunqi Jia, et al. "Ruthenium-catalyzed meta/ortho-selective C–H alkylation of azoarenes using alkyl bromides." Chemical Communications 53, no. 7 (2017): 1261–64. http://dx.doi.org/10.1039/c6cc09323j.

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meta/ortho-Selective C<sub>Ar</sub>–H (di)alkylation reactions of azoarenes have been achieved via [Ru(p-cymene)Cl<sub>2</sub>]<sub>2</sub> catalyzed ortho-metalation using various types of alkyl bromides.

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7

Slocum, D. W., D. Reed, F. Jackson, and C. Friesen. "Media effects in directed ortho metalation." Journal of Organometallic Chemistry 512, no. 1-2 (1996): 265–67. http://dx.doi.org/10.1016/0022-328x(95)05990-7.

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8

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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9

Thiripuranathar, Gobika, Antony P. Y. Chan, Dipendu Mandal, et al. "Double deboronation and homometalation of 1,1′-bis(ortho-carborane)." Dalton Transactions 46, no. 6 (2017): 1811–21. http://dx.doi.org/10.1039/c6dt04457c.

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10

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 alk

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11

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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12

Miah, M. A. Jalil, Mukund P. Sibi, S. Chattopadhyay, Oluwole B. Familoni, and Victor Snieckus. "Directed ortho -Metalation of O -Aryl N ,N -Dialkylcarbamates: Methodology, Anionic ortho -Fries Rearrangement, and Lateral Metalation." European Journal of Organic Chemistry 2018, no. 4 (2017): 440–46. http://dx.doi.org/10.1002/ejoc.201701142.

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13

Cho, Inhee, Labros Meimetis, Lee Belding, Michael J. Katz, Travis Dudding, and Robert Britton. "Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis." Beilstein Journal of Organic Chemistry 7 (September 22, 2011): 1315–22. http://dx.doi.org/10.3762/bjoc.7.154.

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A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxides serve as directed metalation groups. The optimization and scope of this reaction are discussed, and the utility of this process is demonstrated in the one-pot preparation of a number of chiral diols as well as a short synthesis of the chiral ligand Vivol.

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14

Tsukazaki, Masao, and Victor Snieckus. "Directed ortho metalation – radical-induced cyclization synthetic connections. A route to highly substituted benzofurans." Canadian Journal of Chemistry 70, no. 5 (1992): 1486–91. http://dx.doi.org/10.1139/v92-184.

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The synthesis of benzofurans 20a–c, which constitute analogues of 5-lipoxygenase inhibitors 4, is described. The route, representing a potential general method for benzofuran construction, proceeds from phenyl carbamate 11 and involves key directed ortho metalation (11 → 12), anionic ortho-Fries rearrangement (12 → 13a), and radical-induced cyclization (17a–c → 18a–c) steps.

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15

Lau, Stephen YW, and Brian A. Keay. "A highly efficient strategy for the synthesis of 3-substituted salicylic acids by either directed ortho-lithiation or halogenmetal exchange of substituted MOM protected phenols followed by carboxylation." Canadian Journal of Chemistry 79, no. 11 (2001): 1541–45. http://dx.doi.org/10.1139/v01-136.

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A highly efficient synthesis of various 3-substituted salicylic acids is described starting from inexpensive starting materials and requiring no special apparatus.Key words: salicylic acids, ortho-metalation, halogenmetal exchange, methoxymethyl group.

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16

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, le

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17

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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18

Slocum, D. W., and P. Dietzel. "Ortho-metalation of p-chloroanisole: A media study." Tetrahedron Letters 40, no. 10 (1999): 1823–26. http://dx.doi.org/10.1016/s0040-4039(99)00161-6.

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19

Simig, Gyula, and Manfred Schlosser. "ortho-Selective metalation and electrophilic substitution of benzylamine derivatives." Tetrahedron Letters 29, no. 34 (1988): 4277–80. http://dx.doi.org/10.1016/s0040-4039(00)80473-6.

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20

Knochel, Paul, Stefan Wunderlich, Tomke Bresser, Cora Dunst, and Gabriel Monzon. "Efficient Preparation of Polyfunctional Organometallics via Directed ortho-Metalation." Synthesis 2010, no. 15 (2010): 2670–78. http://dx.doi.org/10.1055/s-0029-1218845.

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21

Kramer, Mathias U., Ahmed Yahia, Laurent Maron, and Jun Okuda. "Ortho-metalation of pyridines by cationic yttrium methyl complexes." Comptes Rendus Chimie 13, no. 6-7 (2010): 626–32. http://dx.doi.org/10.1016/j.crci.2010.01.005.

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22

Kauch, Matthias, and Dieter Hoppe. "Synthesis of substituted phenols by directed ortho-lithiation of in situ N-silyl-protected O-aryl N-monoalkylcarbamates." Canadian Journal of Chemistry 79, no. 11 (2001): 1736–46. http://dx.doi.org/10.1139/v01-146.

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A simple, high-yield procedure has been developed for the ortho-lithiation and subsequent ortho-substitution of phenols by a manifold of electrophiles. N,C-Dilithiation of O-aryl N-monoalkylcarbamates proved to be impossible due to a cleavage reaction of the monolithiated intermediates. However, in situ N-silylation of O-aryl N-isopropylcarbamates proceeds smoothly with trialkylsilyl triflates N,N,N',N'-tetramethylethylenediamine (TMEDA). Separation of the formed O-aryl N-isopropyl-N-trialkylsilylcarbamates from the byproduct TMEDA·HOTf, which is insoluble in diethyl ether or toluene, is not

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23

Kersting, Berthold, and Michael DeLion. "Synthesis of Benzisochalcogenol and -azole Derivatives via ortho Metalation of Isophthalamides." Zeitschrift für Naturforschung B 54, no. 8 (1999): 1042–47. http://dx.doi.org/10.1515/znb-1999-0812.

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The syntheses of benzofused isochalcogenazole derivatives via ortho-lithiation of isophthalamides is reported. N ,N′ -Dialkyl-isophthalamides, C6H4-1,3-(CONHR)2, bearing R = iPr or tBu substituents are readily ortho metalated by using 3.3 equiv. of n-BuLi/TMEDA. The organo lithium compounds react with S, Se, or Te to give 2-chalcogenol-isophthalamides, C6H3 -1,3- (CONHR)2-2-XH (X = S, Se, Te). Oxidation of the chalcogenols affords dichalcogenides under acidic and benzisochalcogenazoles under basic conditions, respectively. The formation of the five-membered heterocycles proceeds by disproporti

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24

Baenziger, Markus, Sumesh Eswaran, Yifan Jiang, and Gopu Kasinathan. "Selective ortho-Metalation of a Fluoroarene with Knochel–Hauser Base and Reactions with Various Electrophiles." Synthesis 51, no. 07 (2019): 1649–54. http://dx.doi.org/10.1055/s-0037-1611938.

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Selective ortho-metalation of 1-bromo-2-(1,1-difluoroethyl)-4-fluorobenzene was achieved with the Knochel–Hauser base (TMPMgCl·LiCl) in position 5 of the aromatic ring. The magnesiated intermediate was reacted with a variety of electrophiles to obtain the products in good yields. The work was successfully extended to a Negishi coupling, after transmetalation with ZnCl2 and Pd-catalyzed reaction with 4-iodotoluene.

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25

PLE, N., A. TURCK, K. COUTURE, and G. QUEGUINER. "ChemInform Abstract: Diazines. Part 13. Metalation Without ortho-Directing Group. Functionalization of Diazines via Direct Metalation." ChemInform 26, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199546180.

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26

Mann, André, Jean-Marie Sitamzé, and Camille-Georges Wermuth. "Ortho-directed Metalation of 3-Heterosubstituted 4-Methyl-6-phenylpyridazines." HETEROCYCLES 39, no. 1 (1994): 271. http://dx.doi.org/10.3987/com-94-s(b)22.

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27

Pradhan, Tarun Kanti, Sukhen Chandra Ghosh, and Asish De. "Certain applications of heteroatom directed ortho-metalation in sulfur heterocycles." Arkivoc 2003, no. 9 (2004): 158–73. http://dx.doi.org/10.3998/ark.5550190.0004.919.

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28

Neighbors, Jeffrey D., Maya S. Salnikova, and David F. Wiemer. "Total synthesis of pawhuskin C: a directed ortho metalation approach." Tetrahedron Letters 46, no. 8 (2005): 1321–24. http://dx.doi.org/10.1016/j.tetlet.2004.12.114.

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29

MATSUMOTO, T., H. KAKIGI, and K. SUZUKI. "ChemInform Abstract: Ortho-Metalation of Anthracene Derivative: Problem and Solution." ChemInform 23, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199220253.

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30

Krasutsky, Sergiy, Paul Zhichkin, Catherine Beer, W. Rennells, Seung Lee, and Jin-Ming Xiong. "Preparation of 2-Fluoro-3-aminophenylboronates via Directed ortho-Metalation." Synthesis 2011, no. 10 (2011): 1604–8. http://dx.doi.org/10.1055/s-0030-1260019.

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31

Kondo, Yoshinori, Manabu Shilai, Masanobu Uchiyama, and Takao Sakamoto. "TMP−Zincate as Highly Chemoselective Base for Directed Ortho Metalation." Journal of the American Chemical Society 121, no. 14 (1999): 3539–40. http://dx.doi.org/10.1021/ja984263t.

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32

Brimble, MA, GM Horner, and RJ Stevenson. "Synthesis of Aromatic Spiroacetals." Australian Journal of Chemistry 49, no. 2 (1996): 189. http://dx.doi.org/10.1071/ch9960189.

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The synthesis of aromatic spiroacetal ring systems related to the papulacandins is reported. ortho-Metalation of diisopropylbenzamide, followed by reaction with the electrophiles δ- valerolactone, γ- butyrolactone and γ-valerolactone, provided the keto alcohol adducts (10),(16) and (21) respectively. Reduction of the ketone followed by treatment with acid afforded phthalides (12),(18) and (23). Finally oxidative cyclization with iodobenzene diacetate provided the spiroacetals (7),(14) and (19).

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33

Miah, M. A. Jalil, Mukund P. Sibi, S. Chattopadhyay, Oluwole B. Familoni, and Victor Snieckus. "Directed ortho -Metalation of Aryl Amides, O- Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation." European Journal of Organic Chemistry 2018, no. 4 (2017): 447–54. http://dx.doi.org/10.1002/ejoc.201701143.

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34

Miah, M. A. Jalil, Mukund P. Sibi, S. Chattopadhyay, Oluwole B. Familoni, and Victor Snieckus. "Front Cover: Directed ortho -Metalation of O -Aryl N ,N -Dialkylcarbamates: Methodology, Anionic ortho -Fries Rearrangement, and Lateral Metalation (Eur. J. Org. Chem. 4/2018)." European Journal of Organic Chemistry 2018, no. 4 (2018): 423. http://dx.doi.org/10.1002/ejoc.201800016.

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35

Brimble, Margaret A., and Seng H. Chan. "Synthesis of 7-Methoxy-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-pyran]-3-one and 5,7-Dimethoxy-3′,4′,5′,6′-tetrahydrospiro[isobenzofuran-1(3H),2′-pyran]-3-one." Australian Journal of Chemistry 51, no. 3 (1998): 235. http://dx.doi.org/10.1071/c97193.

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The synthesis of novel aryl spiroketals, which contain a similar substitution pattern to that present in the antifungal agents the papulacandins, is described. Thus, spiroketal (7) was obtained from acid-catalysed cyclization of the keto alcohol (13), and spiroketal (8) was obtained from acid-catalysed cyclization of keto alcohols (12) and (19). Keto alcohols (12), (13) and (19) in turn were prepared by ortho-directed lithiation of amides (10), (11) and oxazoline (17) respectively, followed by reaction with δ-valerolactone. Substitution of the aromatic ring occurred at the sterically hindered

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36

Zani, C. L., A. B. de Oliveira, and V. Snieckus. "Efficient directed ortho metalation-based route to cytotoxic furanonaphthoquinone natural products." Tetrahedron Letters 28, no. 52 (1987): 6561–64. http://dx.doi.org/10.1016/s0040-4039(00)96913-2.

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37

Snieckus, Victor, Francis Beaulieu, Kunihiko Mohri, Wei Han, Christopher K. Murphy, and Franklin A. Davis. "Directed ortho metalation - mediated F+ introduction. Regiospecific synthesis of fluorinated aromatics." Tetrahedron Letters 35, no. 21 (1994): 3465–68. http://dx.doi.org/10.1016/s0040-4039(00)73211-4.

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38

Hillis, Larry R., and Steven J. Gould. "An efficient synthesis of 6-hydroxyanthranilic acid via ortho-directed metalation." Journal of Organic Chemistry 50, no. 5 (1985): 718–19. http://dx.doi.org/10.1021/jo00205a041.

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39

Chau, Nguyet Trang Thanh, Thi Huu Nguyen, Anne-Sophie Castanet, Kim Phi Phung Nguyen, and Jacques Mortier. "Competition of substituents for ortho direction of metalation of veratric acid." Tetrahedron 64, no. 46 (2008): 10552–57. http://dx.doi.org/10.1016/j.tet.2008.08.086.

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40

Sedano, Carlos, Rocío Velasco, Claudia Feberero, Samuel Suárez-Pantiga та Roberto Sanz. "α-Lithiobenzyloxy as a Directed Metalation Group in ortho-Lithiation Reactions". Organic Letters 22, № 16 (2020): 6365–69. http://dx.doi.org/10.1021/acs.orglett.0c02199.

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41

Wunderlich, Stefan H., Tomke Bresser, Cora Dunst, Gabriel Monzon, and Paul Knochel. "ChemInform Abstract: Efficient Preparation of Polyfunctional Organometallics via Directed ortho-Metalation." ChemInform 41, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.201045049.

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42

Schlosser, Manfred, Christophe Heiss, Elena Marzi, and Rosario Scopelliti. "Proton Mobility in 2-Substituted 1,3-Dichlorobenzenes: “ortho” or “meta” Metalation?" European Journal of Organic Chemistry 2006, no. 19 (2006): 4398–404. http://dx.doi.org/10.1002/ejoc.200600350.

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43

Le Fur, Nicolas, Ljubica Mojovic, Nelly Plé, Alain Turck, Vincent Reboul, and Patrick Metzner. "ortho-Metalation of Enantiopure Aromatic Sulfoxides and Stereocontrolled Addition to Imines." Journal of Organic Chemistry 71, no. 7 (2006): 2609–16. http://dx.doi.org/10.1021/jo052358p.

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44

Ye, Heng-Yun, Jing-Lin Chen, and Zhong-Ning Chen. "Oxo-linked diruthenium(III) complex with 2,2′-bipyridine in ortho-metalation." Inorganic Chemistry Communications 10, no. 9 (2007): 1023–25. http://dx.doi.org/10.1016/j.inoche.2007.05.019.

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45

Patel, Jignesh J., Thomas Blackburn, Manlio Alessi, Hannah Sawinski, and Victor Snieckus. "Tetraethylphosphorodiamidate-Directed Metalation Group: Directed Ortho and Remote Metalation, Cross Coupling, and Remote Phospha Anionic Fries Rearrangement Reactions." Organic Letters 22, no. 10 (2020): 3860–64. http://dx.doi.org/10.1021/acs.orglett.0c01123.

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46

Katsuura, K., and V. Snieckus. "Directed ortho metalation reactions. Convergent synthesis of "angular" anthracyclinones ochromycinone and X-14881 C." Canadian Journal of Chemistry 65, no. 1 (1987): 124–30. http://dx.doi.org/10.1139/v87-020.

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Convergent syntheses of the benz[a]anthraquinone natural products X-14881 C (2c) and ochromycinone (2d) have been achieved using aromatic directed metalation strategies. Key steps involve (a) the condensations of dilithiated cis-tetralol (13a) with the aldehydo o-anisamide 14 and of methoxymethyl protected aldehyde 17b with lithiated o-anisamide (18) to give, after acid-catalyzed cyclization, the phthalide 16, and (b) the regiospeciflc hydroxyselenylation of anthraquinone 22 to provide the hydroxyselenide 23.

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47

Hambright, Peter, Ines Batinić-Haberle, and Ivan Spasojević. "Meso tetrakis ortho-, meta-, and para-N-alkylpyridiniopor-phyrins: kinetics of copper(II) and zinc(II) incorporation and zinc porphyrin demetalation." Journal of Porphyrins and Phthalocyanines 07, no. 03 (2003): 139–46. http://dx.doi.org/10.1142/s1088424603000197.

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The relative reactivities of the tetrakis( N -alkylpyridinium- X - yl )-porphyrins where X = 4 (alkyl = methyl, ethyl, n -propyl) , X = 3 (methyl) , and X = 2 (methyl, ethyl, n -propyl, n -butyl, n -hexyl, n -octyl) were studied in aqueous solution. From the ionic strength dependence of the metalation rate constants, the effective charge of a particular cationic porphyrin was usually larger when copper(II) rather than zinc(II) was the reactant. The kinetics of ZnOH + incorporation and the acid catalyzed removal of zinc from the porphyrins in 1.0 M HCl were also studied. In general, the more ba

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48

Mills, Robert J., Nicholas J. Taylor, and Victor Snieckus. "Directed ortho metalation of N,N-diethylbenzamides. Silicon protection of ortho sites and the o-methyl group." Journal of Organic Chemistry 54, no. 18 (1989): 4372–85. http://dx.doi.org/10.1021/jo00279a028.

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49

Cheng, W., and V. Snieckus. "Synthetic connections to the aromatic directed metalation reaction. Iterative ortho metalation-cross coupling tactics for the construction of polyphenyls." Tetrahedron Letters 28, no. 43 (1987): 5097–98. http://dx.doi.org/10.1016/s0040-4039(00)95600-4.

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50

Miah, M. A. J., and V. Snieckus. "Directed ortho metalation of O-pyridyl carbamates. Regiospecific entries into polysubstituted pyridines." Journal of Organic Chemistry 50, no. 25 (1985): 5436–38. http://dx.doi.org/10.1021/jo00225a104.

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