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71749101295
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note
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The ortho-directing ability of methyl ethers is modest (see ref 7a and references therein), whereas ortho substitution of aryl pivalates presents a considerable challenge.
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13
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34447324349
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(a) For a review, see: Snieckus, V. Chem. Rev. 1990, 90, 879.
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For the use of sulfamates in directed metallation reactions and Kumada couplings, see
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(b) For the use of sulfamates in directed metallation reactions and Kumada couplings, see: Macklin, T. K.; Snieckus, V. Org. Lett. 2005, 7, 2519.
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0003412412
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Arenes that possess an -OC(O)R substituent are well-known to undergo electrophilic aromatic substitution to predominantly afford para-substituted products. See: 6th ed.; Wiley: Hoboken, NJ
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Arenes that possess an -OC(O)R substituent are well-known to undergo electrophilic aromatic substitution to predominantly afford para-substituted products. See: Smith, M. B.; March, J. March's Advanced Organic Chemistry, 6th ed.; Wiley: Hoboken, NJ, 2007; p 668.
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0040777702
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2 is now commercially available from Strem Chemicals Inc. (cat. no. 28-0091) and can be prepared in multigram quantities following a simple one-step protocol. See: (a)
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2 is now commercially available from Strem Chemicals Inc. (cat. no. 28-0091) and can be prepared in multigram quantities following a simple one-step protocol. See: (a) Stone, P. J.; Dori, Z. Inorg. Chim. Acta 1971, 5, 434.
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24
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71749113823
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note
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2 is thought to undergo reduction to an active Ni(0) catalyst.
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25
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71749088404
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note
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See the Supporting Information for details.
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28
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33845603147
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29844439845
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For Ni-catalyzed Kumada and Suzuki-Miyaura couplings of aryl fluorides, see: (a)
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For Ni-catalyzed Kumada and Suzuki-Miyaura couplings of aryl fluorides, see: (a) Yoshikai, N.; Mashima, H.; Nakamura, E. J. Am. Chem. Soc. 2005, 127, 17978.
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