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Reaction of 3k in o-DCB at 110°C resulted in incomplete reaction and 4k was obtained in 24% yield with a trace amount of chlorinated byproduct. The formation of chlorinated byproduct was not observed for the reaction of other substrates
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Reaction of 3k in o-DCB at 110°C resulted in incomplete reaction and 4k was obtained in 24% yield with a trace amount of chlorinated byproduct. The formation of chlorinated byproduct was not observed for the reaction of other substrates.
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(a) Terasaka, T.; Tsuji, K.; Kato, T.; Nakanishi, I.; Kinoshita, T.; Kato, Y.; Kuno, M.; Inoue, T.; Tanaka, K.; Nakamura, K. J. Med. Chem. 2005, 48, 4750.
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Kuno, M.7
Inoue, T.8
Tanaka, K.9
Nakamura, K.10
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(b) Harikrishnan, L. S.; Kamau, M. G.; Herpin, T. F.; Morton, G. C.; Liu, Y.; Cooper, C. B.; Salvati, M. E.; Qiao, J. X.; Wang, T. C.; Adam, L. P.; Taylor, D. S.; Chen, A. Y. A.; Yin, X.; Seethala, R.; Peterson, T. L.; Nirschl, D. S.; Miller, A. V.; Weigelt, C. A.; Appiah, K. K.; O'Connell, J. C.; Lawrence, M. R. Bioorg. Med. Chem. Lett. 2008, 18, 2640.
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Cooper, C.B.6
Salvati, M.E.7
Qiao, J.X.8
Wang, T.C.9
Adam, L.P.10
Taylor, D.S.11
Chen, A.Y.A.12
Yin, X.13
Seethala, R.14
Peterson, T.L.15
Nirschl, D.S.16
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Appiah, K.K.19
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We have reported in our previous communication that no kinetic isotope effect was observed in an intramolecular competition experiment using ortho deuterium labeled substrate (see ref 22). This suggests that a hydrogen abstraction step is not involved in the rate determining step and other metalation mechanisms such as σ-bond metathesis might be eliminated. Intramolecular isotope effects are sometimes observed in palladium-catalyzed C-H functionalizations, see:
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We have reported in our previous communication that no kinetic isotope effect was observed in an intramolecular competition experiment using ortho deuterium labeled substrate (see ref 22). This suggests that a hydrogen abstraction step is not involved in the rate determining step and other metalation mechanisms such as σ-bond metathesis might be eliminated. Intramolecular isotope effects are sometimes observed in palladium-catalyzed C-H functionalizations, see: (a) Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084.
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Hennessy, E.J.1
Buchwald, S.L.2
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(b) Shi, Z.; Li, B.; Wan, X.; Cheng, J.; Fang, Z.; Cao, B.; Qin, C.; Wang, Y. Angew. Chem., Int. Ed. 2007, 46, 5554.
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Shi, Z.1
Li, B.2
Wan, X.3
Cheng, J.4
Fang, Z.5
Cao, B.6
Qin, C.7
Wang, Y.8
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(c) Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
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Campeau, L.-C.1
Parisien, M.2
Jean, A.3
Fagnou, K.4
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