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Journal articles on the topic 'Directed Ortho Metalation'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

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

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2

Talko, Alicja, Damian Antoniak, and Michał Barbasiewicz. "Directed ortho-Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates." Synthesis 51, no. 11 (April 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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3

Snieckus, Victor, and Claude Quesnelle. "The Directed ortho Metalation (DoM)–Cross-Coupling Connection: Synthesis of Polyfunctional Biaryls." Synthesis 50, no. 22 (October 5, 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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4

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 (February 1, 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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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 (February 1, 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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6

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 (June 1, 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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7

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 (November 1, 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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8

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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9

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 (May 1, 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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10

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 (December 5, 2017): 440–46. http://dx.doi.org/10.1002/ejoc.201701142.

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11

Knochel, Paul, Stefan Wunderlich, Tomke Bresser, Cora Dunst, and Gabriel Monzon. "Efficient Preparation of Polyfunctional Organometallics via Directed ortho-Metalation." Synthesis 2010, no. 15 (June 29, 2010): 2670–78. http://dx.doi.org/10.1055/s-0029-1218845.

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12

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 (December 5, 2017): 447–54. http://dx.doi.org/10.1002/ejoc.201701143.

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13

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 (April 22, 2020): 3860–64. http://dx.doi.org/10.1021/acs.orglett.0c01123.

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14

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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15

Pradhan, Tarun Kanti, Sukhen Chandra Ghosh, and Asish De. "Certain applications of heteroatom directed ortho-metalation in sulfur heterocycles." Arkivoc 2003, no. 9 (March 24, 2004): 158–73. http://dx.doi.org/10.3998/ark.5550190.0004.919.

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16

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 (February 2005): 1321–24. http://dx.doi.org/10.1016/j.tetlet.2004.12.114.

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17

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 (April 27, 2011): 1604–8. http://dx.doi.org/10.1055/s-0030-1260019.

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18

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 (April 1999): 3539–40. http://dx.doi.org/10.1021/ja984263t.

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19

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 (November 1, 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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20

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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21

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 (May 1994): 3465–68. http://dx.doi.org/10.1016/s0040-4039(00)73211-4.

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22

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 (March 1985): 718–19. http://dx.doi.org/10.1021/jo00205a041.

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23

Sedano, Carlos, Rocío Velasco, Claudia Feberero, Samuel Suárez-Pantiga, and Roberto Sanz. "α-Lithiobenzyloxy as a Directed Metalation Group in ortho-Lithiation Reactions." Organic Letters 22, no. 16 (August 3, 2020): 6365–69. http://dx.doi.org/10.1021/acs.orglett.0c02199.

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24

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 (October 14, 2010): no. http://dx.doi.org/10.1002/chin.201045049.

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25

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 (November 1, 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 required. ortho-Lithiation with n-butyllithiumTMEDA at 78°C leads to the corresponding aryllithium, which does not undergo anionic ortho-Fries rearrangement under the reaction conditions, but is efficiently substituted by electrophilic reagents. During the aqueous work-up, the N-silyl group is removed and the corresponding ortho-substituted O-aryl N-isopropylcarbamate is isolated. Among the introduced electrophiles are: Me3Si, Bu3Sn, PhS, I, Br, Cl, alkyl, α-hydroxyalkyl. Liberation of the free phenols is performed under mild alkaline conditions.Key words: directed ortho-metalation, ortho-lithiated O-aryl carbamates, ortho-substituted phenols, in situ protection of N-monoalkylcarbamates.

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26

Alessi, Manlio, Jignesh J. Patel, Kristina Zumbansen, and Victor Snieckus. "The Tetraethylphosphorodiamidate (OP(O)(NEt2)2) Directed Metalation Group (DMG). Directed ortho and Lateral Metalation and the Phospha Anionic Fries Rearrangement." Organic Letters 22, no. 6 (March 3, 2020): 2147–51. http://dx.doi.org/10.1021/acs.orglett.0c00094.

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27

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 (January 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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28

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 (December 1985): 5436–38. http://dx.doi.org/10.1021/jo00225a104.

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29

Dankwardt, John W. "Directed Ortho Metalation and Facile Anionic Rearrangement of 5-(Aryloxy)-1-phenyltetrazoles." Journal of Organic Chemistry 63, no. 11 (May 1998): 3753–55. http://dx.doi.org/10.1021/jo9718410.

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30

Caron, Stéphane, and Joel M. Hawkins. "Directed Ortho Metalation of Neopentyl Benzoates with LDA: Preparation of Arylboronic Acids." Journal of Organic Chemistry 63, no. 7 (April 1998): 2054–55. http://dx.doi.org/10.1021/jo972141y.

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31

Zhichkin, Paul E., Sergiy G. Krasutsky, Catherine M. Beer, W. Martin Rennells, Seung H. Lee, and Jin-Ming Xiong. "ChemInform Abstract: Preparation of 2-Fluoro-3-aminophenylboronates via Directed ortho-Metalation." ChemInform 42, no. 38 (August 25, 2011): no. http://dx.doi.org/10.1002/chin.201138173.

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32

SITAMZE, J. M., A. MANN, and C. G. WERMUTH. "ChemInform Abstract: ortho-Directed Metalation of 3-Heterosubstituted 4-Methyl-6- phenylpyridazines." ChemInform 26, no. 26 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199526173.

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33

Green, Laine, Brian Chauder, and Victor Snieckus. "ChemInform Abstract: The Directed ortho Metalation - Cross-Coupling Symbiosis in Heteroaromatic Synthesis." ChemInform 31, no. 19 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200019290.

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34

Kondo, Yoshinori, Manabu Shilai, Masanobu Uchiyama, and Takao Sakamoto. "ChemInform Abstract: TMP-Zincate as Highly Chemoselective Base for Directed ortho Metalation." ChemInform 30, no. 34 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199934043.

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35

Stratakis, Manolis. "On the Mechanism of the Ortho-Directed Metalation of Anisole byn-Butyllithium†." Journal of Organic Chemistry 62, no. 10 (May 1997): 3024–25. http://dx.doi.org/10.1021/jo962418e.

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36

Chauder, Brian, Laine Green, and V. Snieckus. "The directed ortho metalation–transition metal–catalyzed reaction symbiosis in heteroaromatic synthesis." Pure and Applied Chemistry 71, no. 8 (August 30, 1999): 1521–29. http://dx.doi.org/10.1351/pac199971081521.

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37

Snieckus, V. "Combined directed ortho metalation-cross coupling strategies. Design for natural product synthesis." Pure and Applied Chemistry 66, no. 10-11 (January 1, 1994): 2155–58. http://dx.doi.org/10.1351/pac199466102155.

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38

Gray, Matthew, Brian J. Chapell, Jakob Felding, Nicholas J. Taylor, and Victor Snieckus. "The Di-t-Butylphosphinyl Directed ortho Metalation Group. Synthesis of Hindered Dialkylarylphosphines." Synlett 1998, no. 4 (April 1998): 422–24. http://dx.doi.org/10.1055/s-1998-1655.

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39

Macklin, Todd K., and Victor Snieckus. "Directed Ortho Metalation Methodology. TheN,N-Dialkyl ArylO-Sulfamate as a New Directed Metalation Group and Cross-Coupling Partner for Grignard Reagents." Organic Letters 7, no. 13 (June 2005): 2519–22. http://dx.doi.org/10.1021/ol050393c.

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40

Metallinos, Costa, Sven Nerdinger, and Victor Snieckus. "N-Cumyl Benzamide, Sulfonamide, and ArylO-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics." Organic Letters 1, no. 8 (October 1999): 1183–86. http://dx.doi.org/10.1021/ol990846b.

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41

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 (September 1989): 4372–85. http://dx.doi.org/10.1021/jo00279a028.

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42

Miao, Bing, Michael Tinkl, and Victor Snieckus. "Directed ortho metalation of ferrocenes. Ring-substituted fulvenes by Nesmeyanov ferrocenylcarbenium ion fragmentation." Tetrahedron Letters 40, no. 13 (March 1999): 2449–52. http://dx.doi.org/10.1016/s0040-4039(99)00246-4.

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43

STAGLIANO, K. W., H. C. MALINAKOVA, and A. TAKAYAMA. "ChemInform Abstract: Synthesis of Contiguously Substituted Nitro Aromatics via Directed ortho-Metalation Nitration." ChemInform 28, no. 37 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199737084.

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44

SNIECKUS, V., F. BEAULIEU, K. MOHRI, W. HAN, C. K. MURPHY, and F. A. DAVIS. "ChemInform Abstract: Directed ortho-Metalation-Mediated F+ Introduction. Regiospecific Synthesis of Fluorinated Aromatics." ChemInform 25, no. 42 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199442080.

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45

Cambie, RC, PI Higgs, KC Lee, MR Metzler, PS Rutledge, RJ Stevenson, and PD Woodgate. "Directed ortho Metalation Studies on Podocarpic Acid Derivatives: Advantageous Use of a LICKOR Base." Australian Journal of Chemistry 44, no. 10 (1991): 1465. http://dx.doi.org/10.1071/ch9911465.

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Methyl 13-(N,N- diethylcarbamoyl )-12-methoxypodocarpa-8,11,13-trien-19-oate (2), 13-(N,N- diethylcarbamoyl )-12,19-dimethoxypodocarpa-8,11,13-triene (8) and N,N-diethyl-2-methoxy-4,5-dimethylbenzamide (15) were prepared for studies involving lithiation directed ortho to the tertiary amide group, in which the use of a LICKOR base was advantageous. Some dynamic features of the n.m.r. spectra of the amides are discussed. Oxazoline derivatives of both tile monocyclic and diterpenoid compounds were synthesized.

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46

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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47

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 (January 10, 2018): 423. http://dx.doi.org/10.1002/ejoc.201800016.

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48

Parsons, Andrew S., Jesus M. Garcia, and Victor A. Snieckus. "Directed ortho metalation reactions. Expedient synthesis of 3,3′-disubstituted 1,1′-bi-(2-phenols) (BIPOLS)." Tetrahedron Letters 35, no. 41 (October 1994): 7537–40. http://dx.doi.org/10.1016/s0040-4039(00)78337-7.

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49

Stagliono, Kenneth W., and Helena C. Malinakova. "Regioselective directed ortho metalation of 3H-naphto[2,1-b]pyrans. Synthesis of methylteretifolione B." Tetrahedron Letters 39, no. 28 (July 1998): 4941–44. http://dx.doi.org/10.1016/s0040-4039(98)00962-9.

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50

Clayden, Jonathan, Hazel Turner, Mark Pickworth, and Thomas Adler. "Ring-Selective Functionalization ofN,N‘-Diarylureas by Regioselective N-Alkylation and Directed Ortho Metalation." Organic Letters 7, no. 15 (July 2005): 3147–50. http://dx.doi.org/10.1021/ol0508025.

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