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39
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79951822111
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note
-
A small amount (ca. 0.060 mmol) of the product of homo-coupling of 2a was observed by GC and GC-MS analyses. The byproduct was readily separated by silica gel column purification. See the Supporting Information for the detailed optimization studies.
-
-
-
-
40
-
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79951845779
-
-
note
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8 remained unsuccessful.
-
-
-
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41
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79951838826
-
-
note
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2 decreased the yield of 3aa by ca. 10%.
-
-
-
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42
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79951845778
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-
note
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The reactions of 1a with benzothiazole, pentafluorobenzene, and 2-chlorothiophene remained unsuccessful.
-
-
-
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43
-
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79951839441
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note
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The KIE value was calculated by considering the partial H/D exchange reaction. The intermolecular KIE implies that C-H cleavage of 2-phenylpyridine would not be involved in the rate-determining step. See the Supporting Information for details.
-
-
-
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44
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2342527678
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For reports of similar KIE values in palladium-catalyzed direct arylation and alkynylation through electrophilic C-H metalation, see: (a)
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For reports of similar KIE values in palladium-catalyzed direct arylation and alkynylation through electrophilic C-H metalation, see: (a) Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
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26444441381
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At this stage, the mechanism of C-H cleavage of phenylazines is not definitive. Thus, the pathway involving concerted metalation-deprotonation as well as σ-bond metathesis also could not be excluded. See: (a)
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At this stage, the mechanism of C-H cleavage of phenylazines is not definitive. Thus, the pathway involving concerted metalation-deprotonation as well as σ-bond metathesis also could not be excluded. See: (a) Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754.
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