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We previously reported a series of Au/Pd cross-coupling reactions that were stoichiometric in Au and catalytic in Pd
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We previously reported a series of Au/Pd cross-coupling reactions that were stoichiometric in Au and catalytic in Pd: Shi, Y.; Ramgren, S. D.; Blum, S. A. Organometallics 2009, 28, 1275.
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While the current manuscript was under revision, another example of a Au/Pd cross-coupling reaction that is also stoichiometric in Au and catalytic in Pd was reported
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While the current manuscript was under revision, another example of a Au/Pd cross-coupling reaction that is also stoichiometric in Au and catalytic in Pd was reported: Hashmi, A. S. K.; Lothschütz, C.; Döpp, R.; Rudolph, M.; Ramamurthi, T. D.; Rominger, F. Angew. Chem., Int. Ed. 2009, 48, 1.
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Recent reports from Nakao and Hiyama and from our group provide examples of the use of this mechanism as a unified concept for reaction design see ref 3 and: A previous example of this mechanistic phenomenon is the Sonogashira reaction (see ref 5)
-
Recent reports from Nakao and Hiyama and from our group provide examples of the use of this mechanism as a unified concept for reaction design (see ref 3 and: Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428) A previous example of this mechanistic phenomenon is the Sonogashira reaction (see ref 5).
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72449164200
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note
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2 did not result in product formation.
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24
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0038102541
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72449151475
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note
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-1 on the basis of triplicate runs at each loading level.
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-
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27
-
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72449189363
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-
note
-
We considered the possibility that cationic 2 rather than neutral 3 was the cross-coupling partner with 4. In the ethyl series, dealkylation of the oxonium ion did not occur, so we could query this point. Cationic ethyl 9 did not participate in cross-coupling, suggesting that neutral 3 rather than cationic 2 was the more likely transmetalation partner:
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28
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59049086003
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Aikawa, H.; Tago, S.; Umetsu, K.; Haginiwa, N.; Asao, N. Tetrahedron 2009, 65, 1774.
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72449207312
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note
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3 did not catalyze this transformation.
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22744442306
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Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
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