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For general references on transition-metal catalysis, see: (a) Cross-coupling Reactions: A Practical Guide; Miyaura, N., Ed.; Springer: New York, 2002. (b) Transition Metal Catalyzed Reactions; Murahashi, S.-I.; Davies, S. G., Eds.; Blackwell Science: Oxford, 1999. (c) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: New York, 1998. (d) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
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For general references on transition-metal catalysis, see: (a) Cross-coupling Reactions: A Practical Guide; Miyaura, N., Ed.; Springer: New York, 2002. (b) Transition Metal Catalyzed Reactions; Murahashi, S.-I.; Davies, S. G., Eds.; Blackwell Science: Oxford, 1999. (c) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: New York, 1998. (d) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
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For general references on transition-metal catalysis, see: (a) Cross-coupling Reactions: A Practical Guide; Miyaura, N., Ed.; Springer: New York, 2002. (b) Transition Metal Catalyzed Reactions; Murahashi, S.-I.; Davies, S. G., Eds.; Blackwell Science: Oxford, 1999. (c) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: New York, 1998. (d) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
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For general references on transition-metal catalysis, see: (a) Cross-coupling Reactions: A Practical Guide; Miyaura, N., Ed.; Springer: New York, 2002. (b) Transition Metal Catalyzed Reactions; Murahashi, S.-I.; Davies, S. G., Eds.; Blackwell Science: Oxford, 1999. (c) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: New York, 1998. (d) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
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Some recent examples with boron-based reagents: (a) Chapman, C. J.; Frost, C. G. Adv. Synth. Catal. 2003, 345. (b) Yamamoto, Y.; Fujita, M.; Miyaura, N. Synlett 2002, 767. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 68, 8944. (d) Hayashi, T.; Senda, T.; Ogaswara, M. J. Am. Chem. Soc. 2000, 122, 10716. (e) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. (f) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
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Some recent examples with boron-based reagents: (a) Chapman, C. J.; Frost, C. G. Adv. Synth. Catal. 2003, 345. (b) Yamamoto, Y.; Fujita, M.; Miyaura, N. Synlett 2002, 767. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 68, 8944. (d) Hayashi, T.; Senda, T.; Ogaswara, M. J. Am. Chem. Soc. 2000, 122, 10716. (e) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. (f) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
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Some recent examples with boron-based reagents: (a) Chapman, C. J.; Frost, C. G. Adv. Synth. Catal. 2003, 345. (b) Yamamoto, Y.; Fujita, M.; Miyaura, N. Synlett 2002, 767. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 68, 8944. (d) Hayashi, T.; Senda, T.; Ogaswara, M. J. Am. Chem. Soc. 2000, 122, 10716. (e) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. (f) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
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4444342672
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note
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Boronic acids and boronate esters readily undergo transmetalation with this catalyst system; there is no noticeable difference in reactivity.
-
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25
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0026600311
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3 group has a conformational free energy (-ΔG°) of 2.4-2.5 kcal/mol, similar to an isopropyl group (2.1 kcal/mol). The value for methyl is 1.8 kcal/mol. See: (a) Nagai, T.; Nishioka, G.; Koyama, M.; Ando, A.; Miki, T.; Kumadaki, I. Chem. Pharm. Bull. 1992, 40, 593. (b) Della, E. W. J. Am. Chem. Soc. 1967, 89, 5221.
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26
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0000880869
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3 group has a conformational free energy (-ΔG°) of 2.4-2.5 kcal/mol, similar to an isopropyl group (2.1 kcal/mol). The value for methyl is 1.8 kcal/mol. See: (a) Nagai, T.; Nishioka, G.; Koyama, M.; Ando, A.; Miki, T.; Kumadaki, I. Chem. Pharm. Bull. 1992, 40, 593. (b) Della, E. W. J. Am. Chem. Soc. 1967, 89, 5221.
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